Maleic Anhydride → 1-Methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thiourea

HRID 1415654Notes

Reaction equation

HRID 1415654 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])=[S:7])=[O:4].[C:16]1(=[O:22])[O:21][C:19](=[O:20])[CH:18]=[CH:17]1>C(O)C>[CH3:1][O:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:22])[CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[S:7])=[O:4]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 3032830Thiophamine

Product 1

HCID 536421621-Methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thioureaYield 28.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-methoxycarbonyl-3-(2-aminophenyl)thiourea (10.9 g., 0.048 mole), maleic anhydride (4.7 g; 0.048 mole) and ethanol (200 ml) was boiled under reflux with stirring for one hour. The clear solution was allowed to cool and the crystals which deposited were filtered off. These were recrystallised once from ethanol and once from a mixture of acetone and petroleum spirit (b.p. 60°-80° C.) to give 1-methoxycarbonyl-3-[2-(3-carboxyacrylamido)phenyl]thiourea (4.4 g) m.p. 170°-173° C. (with decomposition).

Workup

  1. temperatureunder reflux
  2. temperatureto cool
  3. filtrationthe crystals which deposited were filtered off
  4. customThese were recrystallised once from ethanol and once from a mixture of acetone and petroleum spirit (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-4d05abead64c4abab4a08021772a2f2d
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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