Methanethiol → 2-cyanimino-N-(4-methylbenzyl)-thiazolidine

HRID 2290261Notes

Reaction equation

HRID 2290261 reaction equation
CS(=[N:7][C:8]#[N:9])C(=S)OC.[CH3:10][C:11]1[CH:21]=[CH:20][C:14]([CH2:15][NH:16][CH2:17][CH2:18][SH:19])=[CH:13][CH:12]=1.[CH3:22]S>C(O)C>[C:8]([N:7]=[C:22]1[N:16]([CH2:15][C:14]2[CH:20]=[CH:21][C:11]([CH3:10])=[CH:12][CH:13]=2)[CH2:17][CH2:18][S:19]1)#[N:9]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 14306202N-(4-methylbenzyl)-cysteamineHCID 87522899Cyanimino-dithiocarbonic acid dimethylester

Product 1

HCID 143062062-cyanimino-N-(4-methylbenzyl)-thiazolidineYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.65 g (23.5 mmoles) of cyanimino-dithiocarbonic acid dimethylester (purity: 94%) and 5.43 g (30 mmoles) of N-(4-methylbenzyl)-cysteamine are boiled in 30 ml of ethanol until the evolution of methyl-mercaptan terminates (about 2 hours). The reaction mixture is evaporated and the crystalline residue is recrystallized from 6 ml of isopropanol. 4.65 g (85.5%) of 2-cyanimino-N-(4-methylbenzyl)-thiazolidine are obtained, melting at 102° to 104° C.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe crystalline residue is recrystallized from 6 ml of isopropanol

Sources & evidence

ORD record
ord-5fc881085ec445f88922286ca57db4c8
Source dataset
uspto-grants-1986_10
Patent number
US04616025

Reaction notes

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