Dimethylformamide → 5-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N,1,4-trimethyl-1H-pyrrole-2-carboxamide

HRID 1518719Notes

Reaction equation

HRID 1518719 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:29])(=[O:28])[NH2:27])=[CH:22][CH:21]=3)[C:9]=2[CH3:30])=[CH:4][CH:3]=1.[CH3:31][N:32]([CH:34]=O)[CH3:33]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[C:11]([C:14]([N:16]([O:18][CH3:19])[CH3:17])=[O:15])=[C:10]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:28])(=[O:29])[N:27]=[CH:31][N:32]([CH3:34])[CH3:33])=[CH:22][CH:21]=3)[C:9]=2[CH3:30])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 867050305-(4-chlorophenyl)-N-methoxy-N,1,4-trimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxamide

Product 1

HCID 867050315-(4-chlorophenyl)-3-(4-(N-((dimethylamino)methylene)sulfamoyl)phenyl)-N-methoxy-N,1,4-trimethyl-1H-pyrrole-2-carboxamideYield 82.19%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-(4-chlorophenyl)-N-methoxy-N,1,4-trimethyl-3-(4-sulfamoylphenyl)-1H-pyrrole-2-carboxamide (compound 49φ, 0.650 g, 1.45 mmol) in ethyl acetate (12 ml) was added DMF (0.65 ml) and DMF acetal (0.207 g, 0.233 ml, 1.74 mmol) sequentially at room temperature. The reaction mixture was then stirred at room temperature for 15 hr under a nitrogen atmosphere. The progress of the reaction was monitored by TLC. The precipitated out product was filtered and washed with ether (10 ml) to obtain the title compound (0.600 g, 82.19%).

Workup

  1. customThe precipitated out product
  2. filtrationwas filtered
  3. washwashed with ether (10 ml)

Sources & evidence

ORD record
ord-5eb3d2d1106642929fd17aac72054640
Source dataset
uspto-grants-2015_07
Patent number
US09072731B2

Reaction notes

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