Methanethiol → {3-[(4-Methoxyphenyl)methyl]-1,3-thiazolidin-2-ylidene}cyanamide

HRID 2290260Notes

Reaction equation

HRID 2290260 reaction equation
CS(=[N:7][C:8]#[N:9])C(=S)OC.[CH3:10][O:11][C:12]1[CH:22]=[CH:21][C:15]([CH2:16][NH:17][CH2:18][CH2:19][SH:20])=[CH:14][CH:13]=1.[CH3:23]S>C(O)C>[C:8]([N:7]=[C:23]1[N:17]([CH2:16][C:15]2[CH:21]=[CH:22][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH2:18][CH2:19][S:20]1)#[N:9]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 14306201N-(4-methoxybenzyl)-cysteamineHCID 87522899Cyanimino-dithiocarbonic acid dimethylester

Product 1

HCID 14306204{3-[(4-Methoxyphenyl)methyl]-1,3-thiazolidin-2-ylidene}cyanamideYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.65 g (23.5 moles) of cyanimino-dithiocarbonic acid dimethylester (purity: 94%) and 5.91 (30 moles) of N-(4-methoxybenzyl)-cysteamine are boiled in 30 ml of ethanol until the evolution of methyl mercaptan terminates. The reaction mixture is evaporated and the crystalline residue is recrystallized from 15 ml of isopropanol. 5.35 g (92%) of 2-cyanimino-3-(4-methoxybenzyl)-thiazolidine are obtained, melting at 99° to 102° C.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe crystalline residue is recrystallized from 15 ml of isopropanol

Sources & evidence

ORD record
ord-da11e47810b3438c9a5b4916232a9061
Source dataset
uspto-grants-1986_10
Patent number
US04616025

Reaction notes

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