IMIDAZOLE-1-SULFONIC ACID DIMETHYL AMINE

Chemical Properties

IMIDAZOLE-1-SULFONIC ACID DIMETHYL AMINE is Yellow Semi-Solid

Uses

1-(N,N-Dimethylsulfamoyl)-1H-imidazole is an Imidazole (I350200) derivative, used in the preparation of Histamine H3 Receptor Agonists and druglike angiotensin II compounds with affinity for the AT2 receptor.

Uses

1-(Dimethylsulfamoyl)imidazole may be used to synthesize 1-(dimethylsulfamoyl)-2-imidazolecarboxaldehyde.

Uses

IMIDAZOLE-1-SULFONIC ACID DIMETHYL AMINE is an Imidazole (I350200) derivative, used in the preparation of Histamine H3 Receptor Agonists and druglike angiotensin II compounds with affinity for the AT2 r eceptor.

General Description

1-(Dimethylsulfamoyl)imidazole is an imidazole derivative.

Synthesis

The general procedure for the synthesis of N,N-dimethylimidazole-1-sulfonamide from imidazole and N,N-dimethylaminosulfonyl chloride is as follows: with reference to Example 7-1 N,N-dimethyl-1H-imidazole-1-sulfonamide, imidazole (5.00 g, 73.6 mmol) was dissolved in toluene (80 ml), followed by the addition of triethylamine (9.52 ml, 68.4 mmol) and N,N-dimethylaminosulfonyl chloride (6.77 ml, 63.3 mmol). The reaction mixture was stirred at room temperature for 8 hours. After completion of the reaction, the precipitate was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to azeotropic distillation with hexane to give the final N,N-dimethylimidazole-1-sulfonamide (10.9 g, 98% yield). The product was characterized by 1H NMR (CDCl3, 400 MHz) with δ-values of 7.87 (s, 1H), 7.23 (d, 1H, J = 1.4 Hz), 7.11 (d, 1H, J = 1.4 Hz), 2.82 (s, 6H).

References

[1] Patent: EP1647546, 2006, A1. Location in patent: Page/Page column 30
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 481 - 486
[3] Organic Letters, 2005, vol. 7, # 5, p. 929 - 931
[4] Tetrahedron, 2007, vol. 63, # 4, p. 947 - 952
[5] Journal of the Iranian Chemical Society, 2012, vol. 9, # 6, p. 951 - 955