Dibromomethane → 2-(Phenylthiomethylimino)-1,3-dithietane

HRID 436631Notes

Reaction equation

HRID 436631 reaction equation
C(Br)Br.[CH2:4](N(CC)CC)C.[C:11]1([S:17][CH2:18][NH:19][C:20](=[S:22])[S-:21])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[K+].S1CCS1>O.CN(C)C=O>[C:11]1([S:17][CH2:18][N:19]=[C:20]2[S:21][CH2:4][S:22]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 3024DibromomethaneHCID 8471TriethylamineHCID 123092831,2-DithietaneHCID 23667329Potassium phenylthiomethyldithiocarbamate

Product 1

HCID 214533212-(Phenylthiomethylimino)-1,3-dithietane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 28.2 g. of methylene bromide and 10.9 g. of triethylamine in 250 ml. of dimethylformamide was added, in portions, 27.3 g. of potassium phenylthiomethyldithiocarbamate keeping the reaction temperature below 30° C. by cooling. After another two hours, the mixture was poured into water and extracted with ethylene chloride. The ethylene chloride mixture was washed with water, dried, and saturated with dry hydrogen chloride. The resulting salt was collected by filtration and washed with acetone. The salt, on stirring with a mixture of 100 ml. of water and 300 ml. of chloroform, dissolved and removal and concentration of the chloroform layer gave 8.5 g. of the dithietane as a white solid, m.p. 50-52° C.

Workup

  1. additionTo a mixture of 28.2 g
  2. extractionextracted with ethylene chloride
  3. washThe ethylene chloride mixture was washed with water
  4. customdried
  5. filtrationThe resulting salt was collected by filtration
  6. washwashed with acetone
  7. dissolutionof chloroform, dissolved
  8. customremoval and concentration of the chloroform layer
  9. customgave 8.5 g

Sources & evidence

ORD record
ord-3a9b5865a1184520b19cae82fa7a4155
Source dataset
uspto-grants-1977_02
Patent number
US04009279

Reaction notes

Loading…