Dimethylformamide → HCID 21498936, compound

HRID 1730076Notes

Reaction equation

HRID 1730076 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.CN(C)[CH:14]=[O:15].N1(C2[CH2:27][CH2:26][S:25][CH2:24][CH:23]=2)CCCC1>O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][CH:23]2[C:14](=[O:15])[CH2:27][CH2:26][S:25][CH2:24]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Product 1

HCID 21498936HCID 21498936, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 21.7 g (0.10 mole) of 4-fluorophenacyl bromide in 50 ml. of dimethylformamide is added dropwise to a cold stirred solution of 16.9 g (0.10 mole) of 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran [Example 1 (a)], and 100 ml. of dimethylformamide under nitrogen. After 6 hours at ambient temperature, 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. Crystallization and recrystallization from ethanol gives off-white crystals of 3-(4-fluorophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, m.p. 111.5° to 113.5°C.

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. customCrystallization and recrystallization from ethanol

Sources & evidence

ORD record
ord-1f7d618cd3274843a7cc2362dd41b6d7
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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