Dibromomethane → 2-Furfurylimino-1,3-dithietane

HRID 436626Notes

Reaction equation

HRID 436626 reaction equation
[CH2:1]([NH:7][C:8](=[S:10])[S-:9])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH2:11]([NH+](CC)CC)C.C(Br)Br.C(N(CC)CC)C.S1CCS1>CN(C)C=O>[CH2:1]([N:7]=[C:8]1[S:9][CH2:11][S:10]1)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3024DibromomethaneHCID 8471TriethylamineHCID 123092831,2-DithietaneHCID 21453310Triethylammonium furfuryldithiocarbamate

Product 1

HCID 214532962-Furfurylimino-1,3-dithietane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 13.7 g. of triethylammonium furfuryldithiocarbamate, 10.5 ml. of methylene bromide, and 7.0 ml. of triethylamine in 100 ml. of dimethylformamide was stirred for several hours and then poured into ice-water. The oily product was partitioned into ether and the ether mixture was extracted with 3N hydrochloric acid. After extracting the acidic solution with methylene chloride, it was made basic with potassium hydroxide solution and re-extracted with methylene chloride. The methylene chloride mixture, after water washing, drying, and concentrating in vacuo afforded 4.9 g. of the desired dithietane as a yellow oil.

Workup

  1. additionA mixture of 13.7 g
  2. customThe oily product was partitioned into ether
  3. extractionthe ether mixture was extracted with 3N hydrochloric acid
  4. extractionAfter extracting the acidic solution with methylene chloride, it
  5. extractionre-extracted with methylene chloride
  6. dry with materialThe methylene chloride mixture, after water washing, drying
  7. concentrationconcentrating in vacuo
  8. customafforded 4.9 g

Sources & evidence

ORD record
ord-db72441873034a9486531537f026eab8
Source dataset
uspto-grants-1977_02
Patent number
US04009279

Reaction notes

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