O-Phenylenediamine → Thiophamine

HRID 1605505Notes

Reaction equation

HRID 1605505 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

11.7 Parts of methoxycarbonylisothiocyanate is dissolved in 50 parts of benzene and is added to a suspension of 10.8 parts of o-phenylenediamine suspended in 200 parts of benzene at 10°-15°C. The mixture is stirred for 1 hour at room temperature and the product is then removed by filtration yielding 13.7 parts of methyl 4-(o-aminophenyl)-3-thioallophanate, m.p. 182°-183° (D). The melting point is raised to 186°-187° (D) after recrystallization from acetonitrile.

Workup

  1. customthe product is then removed by filtration

Sources & evidence

ORD record
ord-a11317ade703435fbe391f9a5e4223c3
Source dataset
uspto-grants-1976_04
Patent number
US03950391

Reaction notes

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