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

HRID 436629Notes

Reaction equation

HRID 436629 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 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 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-04f2db9f073a4161aed49e48dc89dc23
Source dataset
uspto-grants-1977_02
Patent number
US04009279

Reaction notes

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