Dimethylformamide → HCID 21498932, compound

HRID 1730083Notes

Reaction equation

HRID 1730083 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].N1([C:16]2[CH2:21][CH2:20][S:19](=[O:23])(=[O:22])[CH2:18][CH:17]=2)CCCC1.CN(C)C=[O:27]>O>[CH2:1]([CH:20]1[CH2:21][C:16](=[O:27])[CH2:17][CH2:18][S:19]1(=[O:23])=[O:22])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 21498926HCID 21498926, compound

Product 1

HCID 21498932HCID 21498932, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

22.8 g (0.11 mole) of phenacyl bromide are added dropwise to a cold stirred solution of 23.0 g (0.11 mole) of 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran-1,1-dioxide and 100 ml. of dimethylformamide. The mixture is stirred for 18 hours, diluted with water, and extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated to a solid. Chromatography on silica gel with a benzene and methanol mixture followed by recrystallization from methanol gives colorless crystals of 2-phenacyl-2,3,5,6-tetrahydrothiopyran-4-one- 1,1-dioxide, m.p. 157.5° to 159°C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe chloroform solution is dried over magnesium sulfate
  3. concentrationconcentrated to a solid
  4. customChromatography on silica gel with a benzene and methanol mixture followed by recrystallization from methanol

Sources & evidence

ORD record
ord-a90f9527d5c249cfaa436c9216cbc21e
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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