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

HRID 1973578Notes

Reaction equation

HRID 1973578 reaction equation
C(Br)Br.[CH2:4](N(CC)CC)C.[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([O:16][CH2:17][NH:18][C:19](=[S:21])[S-:20])=[CH:14][CH:13]=1.[K+].S1CCS1>O.CN(C)C=O>[Cl:11][C:12]1[CH:23]=[CH:22][C:15]([O:16][CH2:17][N:18]=[C:19]2[S:20][CH2:4][S:21]2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 3024DibromomethaneHCID 8471TriethylamineHCID 123092831,2-DithietaneHCID 23667330Potassium p-chlorophenoxymethyldithiocarbamate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 19.3 g. of methylene bromide and 3.7 g. of triethylamine in 100 ml. of dimethylformamide was added 10.0 g. of potassium p-chlorophenoxymethyldithiocarbamate in portions. After another one to two 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. waitAfter another one to two hours
  3. custompartitioned into ethylene chloride
  4. filtrationthe resulting salt collected by filtration
  5. customHydrolysis of the salt in a chloroform-water mixture
  6. customfollowed by separation
  7. customdrying
  8. customconcentration of the chloroform layer gave 3.5 g

Sources & evidence

ORD record
ord-839883dbabb94c898f7f946c3057c407
Source dataset
uspto-grants-1976_12
Patent number
US03997668

Reaction notes

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