Phenyl Isothiocyanate → N-(3-Methyl-1,3-thiazolidin-2-ylidene)-N'-phenylthiourea

HRID 1413428Notes

Reaction equation

HRID 1413428 reaction equation
C[O-].[Na+].I.[NH:5]=[C:6]1[N:10]([CH3:11])[CH2:9][CH2:8][S:7]1.[C:12]1([N:18]=[C:19]=[S:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)C>[CH3:11][N:10]1[CH2:9][CH2:8][S:7][C:6]1=[N:5][C:19]([NH:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[S:20]

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 27705073-Methyl-1,3-thiazolidin-2-imine hydroiodideHCID 10942334Sodium Methoxide

Product 1

HCID 54546998N-(3-Methyl-1,3-thiazolidin-2-ylidene)-N'-phenylthiourea

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium methoxide (2.16 g) was added to a mixture of 2-imino-3-methylthiazolidine hydroiodide (10.0 g) in ethanol (50 ml) and brought to reflux, with stirring. Phenylisothiocyanate (5.4 g) in ethanol (20 ml) was added to the mixture over 5 minutes and the resultant mixture heated under reflux, with stirring, for one hour then cooled in ice. Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol.

Workup

  1. temperatureto reflux
  2. temperatureunder reflux
  3. stirringwith stirring, for one hour
  4. temperaturethen cooled in ice
  5. customFilteration gave analytically pure product, mpt 169°-170°, which
  6. custommay be recrystallised from isopropanol

Sources & evidence

ORD record
ord-bbf1b3724acf419abc9d1f16a86dfde4
Source dataset
uspto-grants-1981_02
Patent number
US04250173

Reaction notes

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