Dimethylformamide → HCID 21498918, compound

HRID 1730072Notes

Reaction equation

HRID 1730072 reaction equation
[Br: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>[Br: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 74544-Bromophenacyl bromideHCID 132874681-(3,6-Dihydro-2H-thiopyran-4-yl)pyrrolidine

Product 1

HCID 21498918HCID 21498918, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 41.7 g (0.15 moles) of p-bromophenacyl bromide and 50 ml. of dimethylformamide is added dropwise under nitrogen to a cold stirred solution of 25.4 g (0.15 mole) of 5,6-dihydro-4-(1-pyrrolidinyl)-2H-thiopyran [Example 1 (a)], and 150 ml. of anhydrous dimethylformamide. The reaction mixture is stirred at room temperature for 16 hours, diluted with water, and extracted with chloroform. The chloroform solution is dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel and eluted with a benzene and chloroform mixture. The solid product is recrystallized from ethanol to provide off-white crystals of 3-(4-bromophenacyl)-2,3,5,6-tetrahydrothiopyran-4-one, m.p. 87.5° to 89.5°C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe chloroform solution is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel
  5. washeluted with a benzene and chloroform mixture
  6. customThe solid product is recrystallized from ethanol

Sources & evidence

ORD record
ord-f6c0fa5dfad14c82ac2eb31ad8e59ab8
Source dataset
uspto-grants-1976_11
Patent number
US03991076

Reaction notes

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