p-Chlorothiophenol → 3-[(4-Chlorophenyl)thio]-azacycloheptan-2-one

HRID 358436Notes

Reaction equation

HRID 358436 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.Br[CH:13]1[CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:14]1=[O:15]>CO>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH:13]2[CH2:20][CH2:19][CH2:18][CH2:17][NH:16][C:14]2=[O:15])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 10942334Sodium MethoxideHCID 110306353-Bromoazepan-2-one

Product 1

HCID 132689043-[(4-Chlorophenyl)thio]-azacycloheptan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

54 g (1.0 mol) of sodium methylate and 144.6 g (1.0 mol) of 4-chlorothiophenol are initially introduced into 500 mL of methanol, and a methanolic solution of 192 g (1.0 mol) of α-bromocaprolactam is added dropwise at room temperature. After the exothermic reaction has ceased, the mixture is stirred for a further 3 hours at room temperature, the precipitated sodium bromide is then filtered off under suction and the mother liquor is evaporated down in vacuo. The precipitated crystals are filtered off under suction.

Workup

  1. customAfter the exothermic reaction
  2. filtrationthe precipitated sodium bromide is then filtered off under suction
  3. customthe mother liquor is evaporated down in vacuo
  4. filtrationThe precipitated crystals are filtered off under suction

Sources & evidence

ORD record
ord-c7b72039f4ed450ca9110350fd3d7b5e
Source dataset
uspto-grants-1984_08
Patent number
US04468392

Reaction notes

Loading…