Thiophenol → HCID 22730247, compound

HRID 1785804Notes

Reaction equation

HRID 1785804 reaction equation
Br[CH:2]([C:8]#[N:9])[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:16]1([SH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C.O>[C:8]([CH:2]([S:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4])#[N:9]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 85841Acetamide, 2-bromo-2-cyano-N,N-dimethyl-

Product 1

HCID 22730247HCID 22730247, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-bromo-2-cyano-N,N-dimethylacetamide (3.80 g, 20 mmol), potassium carbonate (2.902 g, 21 mmol) and thiophenol (2.314 g, 21 mmol, 2.16 mL) in acetonitrile (20 mL) was heated to 50° C. for 3 days. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were combined and concentrated. The concentrate was purified by column chromatography on silica gel with 0-50% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 221 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. concentrationconcentrated
  3. customThe concentrate was purified by column chromatography on silica gel with 0-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-91e0b8c67aec484a8510f3c4cc8ce08e
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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