Sodium methanethiolate → 5-methylthio-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362912Notes

Reaction equation

HRID 362912 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-:33])=[O:32])=[C:6]([CH:30]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:8].[CH3:34][S-:35].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:34][S:35][C:2]1[CH:3]=[CH:4][C:5]([N+:31]([O-:33])=[O:32])=[C:6]([CH:30]=1)[C:7]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:8]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 675952155-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 675968055-methylthio-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Step 1): To a solution of 5-fluoro-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (2.0 g, 4.46 mmol) in DMF (10 ml) was added dropwise a solution of sodium thiomethoxide (343 mg, 4.9 mmol) in DMF (10 ml) under stirring at room temperature. After the mixture was stirred overnight, an additional sodium thiomethoxide (34 mg, 0.49 mmol) was added to the mixture. The reaction mixture was diluted with AcOEt and washed twice with H2O. The organic layer was dried over MgSO4 and evaporated to give 5-methylthio-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide as colorless powders, 1.7 g (80%): mp 179°-181° C.

Workup

  1. stirringAfter the mixture was stirred overnight
  2. washwashed twice with H2O
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-0ab7254a759641508782c154aebb2802
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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