Dibromomethane → 2-(p-Chlorophenoxymethylimino)-1,3-dithietane

HRID 1283683Notes

Reaction equation

HRID 1283683 reaction equation
C(Br)Br.[CH3:4]N(C)C=O.[Cl:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][NH:16][C:17](=[S:19])[S-:18])=[CH:12][CH:11]=1.[K+].S1CCS1>O>[Cl:9][C:10]1[CH:21]=[CH:20][C:13]([O:14][CH2:15][N:16]=[C:17]2[S:18][CH2:4][S:19]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 6228DimethylformamideHCID 123092831,2-DithietaneHCID 23667330Potassium p-chlorophenoxymethyldithiocarbamate

Product 1

HCID 214532822-(p-Chlorophenoxymethylimino)-1,3-dithietane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 19.3 g. of methylene bromide and 3.7 g. of treithylamine in 100 ml. of dimethylformamide was added 10.0 g. of potassium p-chlorophenoxymethyldithiocarbamate in portions. After another 1 to 2 hours, the mixture was poured into water and partitioned into ethylene chloride. The dried ethylene chloride mixture was saturated with dry hydrogen chloride and the resulting salt collected by filtration. Hydrolysis of the salt in a chloroform-water mixture followed by separation, drying and concentration of the chloroform layer gave 3.5 g. of the dithietane as pale yellow crystals, m.p. 64.5°-66.0°C.

Workup

  1. additionTo a mixture of 19.3 g
  2. custompartitioned into ethylene chloride
  3. filtrationthe resulting salt collected by filtration
  4. customHydrolysis of the salt in a chloroform-water mixture
  5. customfollowed by separation
  6. customdrying
  7. customconcentration of the chloroform layer gave 3.5 g

Sources & evidence

ORD record
ord-1192a43062624837a2e7ca2e9768e599
Source dataset
uspto-grants-1976_08
Patent number
US03975528

Reaction notes

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