Benzyl mercaptan → HCID 15767064, compound

HRID 275256Notes

Reaction equation

HRID 275256 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[C:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[N:17]=1>CN(C)C=O>[C:8]1([CH2:7][S:14][C:16]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=[C:18]([C:26]([F:27])([F:29])[F:28])[N:17]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 152178453-Pyridinecarboxylic acid, 2-bromo-6-(trifluoromethyl)-, methyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 15767064HCID 15767064, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 6.55 g (0.0584 mol) of potassium-t-butoxide in 60 mL dry dimethylformamide under nitrogen at 0° C. was added 6.84 mL (0.0584 mol) of benzyl mercaptan in 20 mL dimethylformamide while maintaining the temperature below 15° C. A solution of 15.83 g (0.053 mol) of the product from Example 2a or 2b in 20 mL dry dimethylformamide was added dropwise maintaining the temperature at 0° C. and then stirred another 30 minutes at 0° C. The reaction was poured into ice water and extracted with ether. The combined organic layers were washed with water, brine, dried over magnesium sulfate and evaporated to afford 17.84 g (100%). 1H NMR is similar to Example 3. IR (neat) 1725, 1675, 1575, 1135, 850 cm-1.

Workup

  1. temperaturewhile maintaining the temperature below 15° C
  2. extractionextracted with ether
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto afford 17.84 g (100%)

Sources & evidence

ORD record
ord-f190e145516d4019a9a4deead1e7b5cf
Source dataset
uspto-grants-1995_02
Patent number
US05393734

Reaction notes

Loading…