O-Phenylenediamine → Thiophamine

HRID 1076880Notes

Reaction equation

HRID 1076880 reaction equation
[CH3:1][O:2][C:3]([N:5]=[C:6]=[S:7])=[O:4].[C:8]1([NH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14]>C1C=CC=CC=1>[CH3:1][O:2][C:3]([NH:5][C:6]([NH:14][C:9]1[C:8]([NH2:15])=[CH:13][CH:12]=[CH:11][CH:10]=1)=[S:7])=[O:4]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 552246Methoxycarbonyl isothiocyanate

Product 1

HCID 3032830Thiophamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Methyl 4-(o-aminophenyl)-3-thioallophanate is prepared by dissolving 11.7 parts of methoxycarbonyl isothiocyanate in 50 parts of benzene and adding this to 10.8 parts of o-phenylenediamine in 200 parts of benzene at 10° - 15°C. After stirring for one hour at room temperature, 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187°C.(D).

Workup

  1. filtration13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate is recovered by filtration, m.p. 187°C.(D)

Sources & evidence

ORD record
ord-5d008e8d7b8740c18c42e130d39d29e1
Source dataset
uspto-grants-1976_05
Patent number
US03958007

Reaction notes

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