Methyl isothiocyanate → 5-methylthioureidospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one

HRID 894631Notes

Reaction equation

HRID 894631 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3.[CH3:14][N:15]=[C:16]=[S:17]>C(#N)C>[CH3:14][NH:15][C:16](=[S:17])[NH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C:7]3([C:10](=[O:11])[C:4]=2[CH:3]=1)[CH2:9][CH2:8]3

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 12925991HCID 12925991, compound

Product 1

HCID 129260365-methylthioureidospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-oneYield 65.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Aminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (1.75 g.) and methyl isothiocyanate (1.1 g.) were stirred in acetonitrile (60 ml.) at room temperature for 15 hours, and then the mixture was refluxed under heating for 3 hours. The solvent was evaporated off under reduced pressure, and the residue was recrystallized from methanol to give yellow prisms of 5-methylthioureidospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (1.62 g.). m.p. 191°-194° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-3b06025a55864a138c7bd12a38ff3c24
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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