Water → HCID 58096340, compound

HRID 1968678Notes

Reaction equation

HRID 1968678 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:10]([N:13]([CH3:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[NH:8][CH3:9].C(N(CC)CC)C.[Cl:28][CH2:29][CH2:30][C:31](Cl)=[O:32].O>CN(C)C=O.C(#N)C>[Cl:28][CH2:29][CH2:30][C:31]([NH:1][C:2]1[CH:3]=[C:4]([S:10](=[O:12])(=[O:11])[N:13]([CH3:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[NH:8][CH3:9])=[O:32]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 58096311HCID 58096311, compound

Product 1

HCID 58096340HCID 58096340, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-amino-N-methyl-4-(methylamino)-N-phenylbenzene sulfonamide (5.4 g, 0.018 mol) and triethylamine (1.81 g, 0.018 mol) in dimethylformamide (16 ml) being cooled on ice (˜5° C.), chloropropionyl chloride (2.32 g, 0.018 mol) was added. The reaction was stirred at room temperature for 5 h. Thereupon, water (14 ml) and acetonitrile (5 ml) were added for 5 h. The precipitate formed was filtered. The yield of 3-chloro-N-(5-(N-methyl-N-phenylsulfamoyl)-2-(methylamino)phenyl)propanamide was 3.1 g (45%).

Workup

  1. additionwas added
  2. customThe precipitate formed
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-cf33d738eed54b50a3c650c106ffba46
Source dataset
uspto-grants-2013_04
Patent number
US08426433B2

Reaction notes

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