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

HRID 1973580Notes

Reaction equation

HRID 1973580 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-db8ffea6e4bc4bf69032e10b311aa933
Source dataset
uspto-grants-1976_12
Patent number
US03997668

Reaction notes

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