Dimethylformamide → HCID 21498935, compound

HRID 1730070Notes

Reaction equation

HRID 1730070 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].CN(C)[CH:13]=[O:14].N1(C2[CH2:26][CH2:25][S:24][CH2:23][CH:22]=2)CCCC1>O>[CH2:1]([CH:22]1[C:13](=[O:14])[CH2:26][CH2:25][S:24][CH2:23]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 6259Phenacyl bromideHCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Product 1

HCID 21498935HCID 21498935, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 56.3 g (0.28 mole) of phenacyl bromide in 100 ml. of dimethylformamide is added dropwise during 20 minutes under nitrogen to a cold stirred solution of 47.6 g (0.28 mole) of 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran and 300 ml. of anhydrous dimethylformamide. After 2 hours, the solution is diluted with H2O and extracted with chloroform. The chloroform solution is washed with water, dried over magnesium sulfate and concentrated. The product is crystallized from ethanol to give crystals of 3-phenacyl-2,3,5,6-tetrahydrothiopyran-4-one. This is recrystallized from ethanol to yield crystals; m.p. 101.5° to 103.5° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe product is crystallized from ethanol

Sources & evidence

ORD record
ord-3a96b2aec49b4e048b9e045afcf22639
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

Loading…