Water → HCID 10981772, compound

HRID 1824590Notes

Reaction equation

HRID 1824590 reaction equation
NC1[C:3]([Cl:23])=[CH:4][C:5]([N+:20]([O-:22])=[O:21])=[C:6]([S:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])[CH3:14])=O)[CH:7]=1.CI.C(=O)([O-])[O-].[K+].[K+].[OH2:32].[CH3:33][N:34]([CH:36]=O)[CH3:35]>>[Cl:23][C:3]1[C:36]([N:34]([CH3:35])[CH3:33])=[CH:7][C:6]([S:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])[CH3:14])=[O:32])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11046378HCID 11046378, compound

Product 1

HCID 10981772HCID 10981772, compoundYield 65%

Procedure

2-(5-Amino-4-chloro-2-nitro-phenylthio)-N,N-dimethyl-benzamide (18) (1.0 g, 2.84 mmol) was heated to reflux with methyl iodide 1.0 g) and potassium carbonate (5 g) in 10 mL of anhydrous DMF for 24 h. The mixture was poured into cold water and the precipitate was collected by filtration and purified by silica gel chromatography to yield 22 (Yellow powder, 0.7 g, 65%): IR (cm−1, neat) 2923, 1636, 1577, 1498, 1322, 1299; 1H NMR (200 MHz CDCl3) δ 8.23 (s. 1H), 7.4–7.6 (m, 4H), 6.20 (s, 1H), 3.04 (s, 3H), 2.82 (s, 3H), 2.71 (s, 6H). Anal. (C17H18ClN3O3S-0.5 H2O) C, H, N.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-fa86691259ea47838178aa925d603dde
Source dataset
uspto-grants-2006_05
Patent number
US07041851B2

Reaction notes

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