Dimethylformamide → HCID 21498937, compound

HRID 1730082Notes

Reaction equation

HRID 1730082 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[O:9])[CH2:7]Br.CN(C)[CH:17]=[O:18].N1(C2[CH2:30][CH2:29][S:28][CH2:27][CH:26]=2)CCCC1>O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[O:9])[CH2:7][CH:26]1[C:17](=[O:18])[CH2:30][CH2:29][S:28][CH2:27]1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-oneHCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Product 1

HCID 21498937HCID 21498937, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 32.6 g of m-trifluoromethylphenacyl bromide in 10 ml. of dimethylformamide is added dropwise to a stirred solution of 20 g (0.12 mole of 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran [Example 1 (a)] and 100 ml. of dimethylformamide. After 2 hours, the mixture is diluted with water and extracted with chloroform. The chloroform solution is washed with water, dried over magnesium sulfate, and concentrated to an oil. The oil is chromatographed on silica gel with benzene and chloroform mixtures to give 2,3,5,6-tetrahydro-3-(3-trifluoromethylphenacyl)thiopyran-4-one as an oil. Infrared and nuclear magnetic resonance spectra are consistent with the assigned structure.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customThe oil is chromatographed on silica gel with benzene and chloroform mixtures

Sources & evidence

ORD record
ord-fcf15b98a9d4495daa18992d3fc22891
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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