Sodium hydride → HCID 24964377, compound

Reaction equation

[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.[H-].[Na+].[CH2:13]([N:23]=[C:24]=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22]>CN(C)C=O>[CH2:13]([NH:23][C:24]([NH:10][S:7]([C:4]1[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=1)(=[O:9])=[O:8])=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([NH:10][S:7]([C:4]1[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=1)(=[O:9])=[O:8])=[O:22]

Participants

Procedure

To a solution of 0.35 g 5-methyl-thiophene-3-sulfonic acid amide (example 46a) in 10 ml dimethylformamide was added 0.080 g sodium hydride 55% in oil and the mixture was stirred at room temperature for 30 min. To the resulting solution was added dropwise 0.180 g heptamethylene diisocyanate (CAS18020-78-5) and the mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The phases were separated and the aqueous phase was washed with ethyl acetate and purified by chromatography on 100 ml MCl gel with a gradient (water 0-50% acetonitrile) The product fractions were collected and the product was precipitated by adjusting the pH to 2.00 by addition of 1N hydrochloric acid. The solid was collected by filtration and washed with water and dried to constant weight to yield 0.24 g of the title compound as white powder. MS (ISN) M−H+=536.0