Water → 2-Thioxo-[1,3]dithiole-4-carboxylic acid methyl ester

HRID 1682092Notes

Reaction equation

HRID 1682092 reaction equation
[S:1]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](C(OC)=O)[S:3][C:2]1=[S:14].O.[Br-].[Li+].O>CN(C)P(=O)(N(C)C)N(C)C>[S:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[S:1][C:2]1=[S:14]

Participants

5

Reactant 3

HCID 962WaterHCID 547914Dimethyl 2-thioxo-1,3-dithiole-4,5-dicarboxylateHCID 23702478Lithium bromide hydrate

Product 1

HCID 108671782-Thioxo-[1,3]dithiole-4-carboxylic acid methyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

30 Grams (0.12 mol) of dimethyl 1,3-dithiol-2-thion-4,5-dicarboxylate synthesized according to the method of G. C. Papavassiliou, et al [Synthetic Metals, Vol. 27 (1988) B-373-B378] was dissolved in 30 ml of hexamethylphosphorictriamide (HMPA), and 12.6 g (0.12 mol) of lithium bromide monohydrate was added. The resultant mixture was heated at 60° C. for 1 hour, the reaction mixture was allowed to cool to room temperature, 200 ml of water was added, and a yellow solid formed was separated by filtering and washed with water. The solid obtained was dried and recrystallized from carbon tetrachloride to give 16.2 g of yellow acicular crystals of methyl 1,3-dithiol-2-thione-4-carboxylate (yield 70%).

Workup

  1. customa yellow solid formed
  2. customwas separated
  3. filtrationby filtering
  4. washwashed with water
  5. customThe solid obtained
  6. customwas dried
  7. customrecrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-f386a8c6f8bd459a858c1a15a2649769
Source dataset
uspto-grants-1992_12
Patent number
US05175280

Reaction notes

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