Iodoacetamide → HCID 66889616, compound

HRID 1162429Notes

Reaction equation

HRID 1162429 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[N:16]=[N:15][C:14]([NH:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:13][CH:12]=1.I[CH2:29][C:30]([NH2:32])=[O:31]>CN(C=O)C.O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14](=[N:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[N:15]([CH2:29][C:30]([NH2:32])=[O:31])[N:16]=1

Participants

6

Reactant 3

HCID 3727IodoacetamideHCID 81531DiisopropylethylamineHCID 3153536N-(6-chloropyridazin-3-yl)-4-methylbenzenesulfonamide

Product 1

HCID 66889616HCID 66889616, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (10.4 mL, 81 mmol) was added to a suspension of N-(6-chloropyridazin-3-yl)-4-methylbenzenesulfonamide (21 g, 74 mmol) in dry DMF (100 mL) under argon. To the resulting solution was added 2-iodoacetamide (15 g, 81 mmol, Aldrich, St. Louis, Mo.) and the mixture was stirred for 24 h at rt. The reaction mixture was diluted with water and precipitated solid was filtered off to afford the title compound (17 g, 68%). 1H NMR (DMSO-d6, 300 MHz): δ 2.4 (s, 3H), 4.8 (s, 2H), 7.3 (d, 2H), 7.6-7.8 (m, 4H), 7.95 (d, 1H).

Workup

  1. customprecipitated solid
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-3dc01bdbbcf94553afe286de30b52071
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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