Water → HCID 53743338, compound

HRID 967879Notes

Reaction equation

HRID 967879 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:31])=[C:16]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH:17]=1)=[O:10])(=[O:4])=[O:3].[H-].[Na+].[CH3:37]I.O>CN(C=O)C>[CH3:37][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=1)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:31])=[C:16]([NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH:17]=1)=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22291038HCID 22291038, compound

Product 1

HCID 53743338HCID 53743338, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-[5-(3-methanesulphonylaminobenzamido)-2-methylphenyl]-3,4-dimethoxybenzamide (0.3 g) in DMF (5 ml) was added portionwise to a stirred mixture of sodium hydride (0.025 g) in DMF (5 ml). The resultant mixture was stirred at ambient temperature for 40 minutes. Methyl iodide (0.088 g) was added and the mixture was stirred at ambient temperature for 3 hours. The mixture was poured into water (150 ml). The resultant 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 (0.18 g); m.p. 168-169° C.; NMR Spectrum: (DMSOd6) 2.19 (s, 3H), 2.99 (s, 3H), 3.82 (s, 6H), 7.07 (d, 1H), 7.21 (d, 1H). 7.59 (m, 5H), 7.79 (s, 1H), 7.87 (d, 1H), 7.93 (s, 1H), 9.75 (br s, 1H), 10.25 (br s, 1H); Mass Spectrum: M+H+ 498.

Sources & evidence

ORD record
ord-83144add385b47bf842933f0c1792e1b
Source dataset
uspto-grants-2005_10
Patent number
US06956037B2

Reaction notes

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