Reactions of sulphonyl chloride–NN-dimethylformamide complexes

Albright, J. Donald; Benz, E.; Lanzilotti, A. E.; Goldman, Leon

doi:10.1039/c19650000413

Cited by 7 publications

(2 citation statements)

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“…This meant that the presence of DMF was detrimental, most likely because of its reactivity with MsCl to form sulfonyl chloride-N,N-dimethylformamide complexes. 42,43 Due to the poor solubility of 2 in most inert solvents, we used a minimum amount of DMF, just enough to dissolve 2 and DCM as the bulk solvent. Regulating the ratio of DMF to reagents was important.…”

Section: ■ Results and Discussionmentioning

confidence: 95%

Multistep Continuous Flow Synthesis of Stavudine

et al. 2021

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Herein, we demonstrate an elegant multistep continuous flow synthesis for stavudine (d4T), a potent nucleoside chemotherapeutic agent for human immunodeficiency virus, acquired immunodeficiency syndrome (AIDS) and AIDS-related conditions. This was accomplished via six chemical transformations in five sequential continuous flow reactors from an affordable starting material, 5-methyluridine. In the first instance, single step continuous flow synthesis was demonstrated with an average of 97% yield, 21.4 g/h throughput per step, and a total of 15.5 min residence time. Finally, multistep continuous flow synthesis of d4T in 87% total yield with a total residence time of 19.9 min and 117 mg/h throughput without intermediate purification was demonstrated.

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Section: ■ Results and Discussionmentioning

confidence: 95%

Multistep Continuous Flow Synthesis of Stavudine

et al. 2021

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“…Treatment of p -nitrobenzyl alcohol with N,N -dimethylformamide (DMF) instead of dichloromethane, resulted in the formation of p -nitrobenzyl chloride in 87% yield, according to [5]. The results could be explained by the effect that DMF as the polar aprotic solvent accelerated the nucleophilic substitution reaction.…”

Section: Resultsmentioning

confidence: 99%

Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates

Ding

Wang

et al. 2011

Molecules

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Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.

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Methods of formation of the carbon‐nitrogen double bond

Dayagi

Degani

1970

PATAI'S Chemistry of Functional Groups

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Reactions of sulphonyl chloride–NN-dimethylformamide complexes

Cited by 7 publications

References 0 publications

Multistep Continuous Flow Synthesis of Stavudine

Multistep Continuous Flow Synthesis of Stavudine

Treatment of Alcohols with Tosyl Chloride Does Not always Lead to the Formation of Tosylates

Methods of formation of the carbon‐nitrogen double bond

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