Sulfurierungen XII. Über den Sulfurierungsmechanismus von Anilin mit Schwefelsäure

Vrba, Z.; Allan, Z. J.

doi:10.1135/cccc19682502

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“…Sulfamide and Cyclic Compound SynthesesThe reaction of amines, both alkyl and aryl, with sulfamyl chlorides is a general route to the synthesis of sulfamides. RR1NS02CI + NH2R2 -RR1NS02NHR2(98) R1 = R2 = R = alkyl Monoor dialkylsulfamyl chlorides are generally used with alkyl groups in the range C,_3. A wide range of sulfamides have been prepared, including a-(aminoalkyl)-4-hydroxy-3-(sulfamylamino)benzyl alcohols517'519 (adrenergic stimulants), sulfamido-phenethanolamines520 (antiarrhythmic agents), 2-(aminobenzimidazole)sulfonamides521 (fungicides), and N,N'-substituted sulfamides522 (herbicides).Cohen and Klarberg,523 Hamprecht,524-5278 and Bancroft et al527b demonstrated the synthetic usefulness of sulfamyl chlorides in the preparation of heterocyclic compounds such as 2,1,3benzothiadiazin-4-one 2,2-dioxides (151).…”

mentioning

confidence: 99%

Sulfamic acid and its N-substituted derivatives

Benson¹,

Spillane²

1980

Chem. Rev.

115

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mentioning

confidence: 99%

Sulfamic acid and its N-substituted derivatives

Benson¹,

Spillane²

1980

Chem. Rev.

115

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References

1971

Organic Chemistry

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Studies of Reactions of Amines with Sulfur Trioxide. VI. Thermal Reactions of Anilinium, Dimethylanilinium, and Trimethylanilinium Salts of Butylamidosulfuric Acid

Kanetani¹,

Yamaguchi²

1981

Bulletin of the Chemical Society of Japan

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When the title compounds were heated in an evacuated reaction vessel, both transsulfonation and rearrangement occurred. At lower temperatures (80–120 °C) the corresponding phenylamidosulfates and sulfophenylamidosulfates (transsulfonation products) were the main products. Increasing temperature led to the formation of ring mono- and disulfonates (rearrangement products) at the expense of the transsulfonation products. The sulfonate group always migrated to the ortho and/or para position(s) to the amino group. In no case was any meta-product detected. There was no significant difference in the ease of transsulfonation among the anilinium salts studied except 2,6-dimethyl- and 2,4,6-trimethylanilinium salts. On the other hand, the ease of rearrangement and the orientation of ring sulfonation depended strongly on the structure of the substrate anilines. The thermal reactions of 2,4,6-trimethylanilinium butylamidosulfate produced (2,4,6-trimethylphenylimido)bis(sulfate) in addition to (2,4,6-trimethylphenylamido)sulfate. This is the first isolation of an arylimidobis(sulfate) from such reactions. Mechanisms of the transsulfonation and the rearrangement have been discussed.

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Sulfurierungen XII. Über den Sulfurierungsmechanismus von Anilin mit Schwefelsäure

Cited by 3 publications

References 0 publications

Sulfamic acid and its N-substituted derivatives

Sulfamic acid and its N-substituted derivatives

References

Studies of Reactions of Amines with Sulfur Trioxide. VI. Thermal Reactions of Anilinium, Dimethylanilinium, and Trimethylanilinium Salts of Butylamidosulfuric Acid

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