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

HRID 1053287Notes

Reaction equation

HRID 1053287 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-carboxamide2×

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 49, 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-2581529af07f47ce9882b5c7fe409d24
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

Loading…