Dimethylformamide → HCID 21498910, compound

HRID 1730080Notes

Reaction equation

HRID 1730080 reaction equation
[Cl: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>[Cl: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 68303p-Chlorophenacyl bromideHCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Product 1

HCID 21498910HCID 21498910, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 23.4 g (0.10 mole) of p-chlorophenacyl bromide in 50 ml. of dimethylformamide is added dropwise under nitrogen to a 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. 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. The oil is chromatographed on silica gel and eluted with benzene and chloroform mixtures to give an oil which solidifies. The resulting solid is recrystallized from ethanol to give off-white crystals of 3-(4-chlorophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, m.p. 78° to 81°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. customThe oil is chromatographed on silica gel
  6. washeluted with benzene and chloroform mixtures
  7. customto give an oil which
  8. customThe resulting solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-f903c5310c1947588f70c4f3ea6f6ac2
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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