Benzyl mercaptan → HCID 15767064, compound

HRID 275255Notes

Reaction equation

HRID 275255 reaction equation
[H-].[Na+].[CH2:3]([SH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[C:12]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[N:13]=1>CN(C)C=O>[C:4]1([CH2:3][S:10][C:12]2[C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=[C:14]([C:22]([F:23])([F:25])[F:24])[N:13]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 152178453-Pyridinecarboxylic acid, 2-bromo-6-(trifluoromethyl)-, methyl ester

Product 1

HCID 15767064HCID 15767064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 0.28 g (0.008 mol) of 60% sodium hydride (in mineral oil, then washed with hexanes) in 7 mL dry dimethylformamide under nitrogen at 0° C. was added 0.8 mL (0.0067 mol) of benzyl mercaptan while maintaining the temperature below 10° C. The suspension was warmed to room temperature and stirred another 45 minutes before cooling back to 0° C. A solution of 2.0 g (0.0067 mol) of the product from Example 2a or 2b in 5 mL dry dimethylformamide was added dropwise and stirred 30 minutes at 0° C. The reaction was poured into ice water and extracted with ether. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated to afford 2.3 g (100%). 1H NMR (CDCl3) δ, 3.94 (3H, s), 4.43 (2H, s), 7.2-7.6 (6H, m), 8.38 (1H, d, J=8Hz).

Workup

  1. washwashed with hexanes) in 7 mL dry dimethylformamide under nitrogen at 0° C.
  2. temperaturewhile maintaining the temperature below 10° C
  3. temperaturebefore cooling back to 0° C
  4. stirringstirred 30 minutes at 0° C
  5. extractionextracted with ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto afford 2.3 g (100%)

Sources & evidence

ORD record
ord-2f70d41570504e0aaec307e2838ce542
Source dataset
uspto-grants-1995_02
Patent number
US05393734

Reaction notes

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