Diethyl Ether → N-(3-Methyl-1,3-thiazolidin-2-ylidene)-N'-phenylthiourea

HRID 1649044Notes

Reaction equation

HRID 1649044 reaction equation
[NH:1]=[C:2]1[N:6]([CH3:7])[CH2:5][CH2:4][S:3]1.[C:8]1([N:14]=[C:15]=[S:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCOCC>C1C=CC=CC=1>[CH3:7][N:6]1[CH2:5][CH2:4][S:3][C:2]1=[N:1][C:15]([NH:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[S:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7673Phenyl IsothiocyanateHCID 773183-Methyl-1,3-thiazolidin-2-imine

Product 1

HCID 54546998N-(3-Methyl-1,3-thiazolidin-2-ylidene)-N'-phenylthioureaYield 75%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 0.043 mole of 2-imino-3-methylthiazolidine and an equimolar amount of phenylisothiocyanate in 70 ml of dry benzene is refluxed under nitrogen for 2.5 hours. Some ether is added to the cooled reaction mixture and solids are filtered off, 9.8 g (90%). Recrystallization from acetonitrile-ether (1:1) gives 8.0 g (75%) of pure N-(3-methyl-2-thiazolidinylidene)-N'-phenylthiourea; m.p. 168.5°-170.5° C.

Workup

  1. filtrationare filtered off
  2. customRecrystallization from acetonitrile-ether (1:1)

Sources & evidence

ORD record
ord-48d0ad4196374bd6a78daf7039b1f5b7
Source dataset
uspto-grants-1983_11
Patent number
US04414211

Reaction notes

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