Dimethylformamide → HCID 17922787, compound

HRID 1369519Notes

Reaction equation

HRID 1369519 reaction equation
CI.[CH3:3][N:4]([CH3:35])[C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][CH:34]=1)[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:31])=[C:15]([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:20]=2)[CH:16]=1)=[O:9].[C:36](=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH3:35][N:4]([CH3:3])[C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][CH:34]=1)[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:31])=[C:15]([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]([S:26]([CH3:29])(=[O:28])=[O:27])[CH3:36])[CH:20]=2)[CH:16]=1)=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22291070HCID 22291070, compound

Product 1

HCID 17922787HCID 17922787, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl iodide (0.1 g) was added to a mixture of N-[5-(3-dimethylaminobenzamido)-2-methylphenyl]-3-methanesulphonylaminobenzamide (0.3 g), caesium carbonate (0.23 g) and DMF (20 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The reaction mixture was poured into water (250 ml). The precipitate was isolated, washed in turn with water and diethyl ether and dried under vacuum at 60° C. There was thus obtained the title compound (0.23 g); m.p. 168-169° C.; NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.95 (s, 6H), 3.0 (s, 3H), 6.9 (d, 1H), 7.21 (m, 3H), 7.29 (t, 1H), 7.58 (m, 3H), 7.81 (d, 1H), 7.9 (d, 1H), 7.98 (d, 1H) 9.97 (br s, 1H), 10.09 (br s, 1 H); Mass Spectrum: M+H+ 481.

Workup

  1. customThe precipitate was isolated
  2. washwashed in turn with water and diethyl ether
  3. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-156fc82485fc42fab9b32ed0d794cf2c
Source dataset
uspto-grants-2003_06
Patent number
US06579872B1

Reaction notes

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