Dimethyl Sulfoxide → HCID 178489969, compound

HRID 1485974Notes

Reaction equation

HRID 1485974 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:21]1C=[N:23][C:24](Cl)=[CH:25][C:26]=1[CH3:27].[CH3:29][S-].[Na+].C[S:33]([CH3:35])=O>>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:21]1[C:35]([SH:33])=[N:23][C:24]([CH3:29])=[CH:25][C:26]=1[CH3:27]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4378561Sodium methanethiolateHCID 86642576HCID 86642576, compound

Product 1

HCID 178489969HCID 178489969, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-N-(2-methoxy-6-methyl-phenyl)-N-methyl-benzamide 2-31 (20.0 mg, 0.048 mmol) and sodium thiomethoxide (3.3 mg, 0.048 mmol) in DMSO (1 mL) was heated at 80° C. for 1 hr. The mixture was partitioned between ethyl acetate and water. The organic layer was separated and purified by HPLC yielding 4-chloro-N-(2-methoxy-6-methyl-phenyl)-N-methyl-3-(4-methyl-6-methyl-sulfanylpyridin-3-yl)-benzamide (4.3 mg). MS (M+H)+: 426.9; tR=7.92 min. (method 2).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-b0d088e987604e11bb5a88b27695286b
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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