1,1-Bis(methylthio)-2-nitroethylene → 3-Benzyl-2-nitromethylene-thiazolidine

HRID 2290259Notes

Reaction equation

HRID 2290259 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][SH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS[C:14](SC)=[CH:15][N+:16]([O-:18])=[O:17]>C(O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][S:11][C:14]1=[CH:15][N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 136802Ethanethiol, 2-benzylamino-

Product 1

HCID 30243963-Benzyl-2-nitromethylene-thiazolidineYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.34 g (20 moles) of N-benzyl-cysteamine and 3.3 g of 1,1-bis-methylthio-2-nitro-ethylene are refluxed in 50 ml of ethanol for one hour. The gas evolution terminates after boiling for 20 minutes. The mixture is cooled and the precipitated product is isolated by filtration. 4.52 g of 3-benzyl-2-nitromethylene-thiazolidine are obtained, melting at 136° to 138° C. Crystallization of the product from 140 ml of ethanol yields 4.08 g of a purified product, melting at 139° C.

Workup

  1. temperatureThe mixture is cooled
  2. customthe precipitated product is isolated by filtration

Sources & evidence

ORD record
ord-7cdd1e28a5fc45739c3ae95110efa5e3
Source dataset
uspto-grants-1986_10
Patent number
US04616025

Reaction notes

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