Phenyl Isothiocyanate → HCID 21427813, compound

HRID 437521Notes

Reaction equation

HRID 437521 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.[C:16]1([N:22]=[C:23]=[S:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[C:16]1([NH:22][C:23](=[S:24])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14])=[CH:6][CH:7]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 11148694HCID 11148694, compound

Product 1

HCID 21427813HCID 21427813, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-Aminophenyl)-1-trifluoroacetylhydrazine (2.0 g, 0.0091 mole) and phenyl isothiocyanate (1.2 g, 0.0091 mole) were mixed together in ethanol (25 ml) and the mixture was heated to reflux for 20 minutes. A white solid precipitated out of the mixture during the heating. The mixture was chilled in ice and the solid was filtered off, washed with ethanol, and dried. Spectral data on this material indicated that it was not the desired product. The filtrate from above was diluted with water and a second solid material formed. This material was filtered off, washed with water and dried to give a white crystalline powder. Yield 0.80 g (25%), m.p. 172°-174° C. Spectral evidence verified that this substance was the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 20 minutes
  3. customA white solid precipitated out of the mixture during the heating
  4. temperatureThe mixture was chilled in ice
  5. filtrationthe solid was filtered off
  6. washwashed with ethanol
  7. customdried
  8. additionThe filtrate from above was diluted with water
  9. customa second solid material formed
  10. filtrationThis material was filtered off
  11. washwashed with water
  12. customdried
  13. customto give a white crystalline powder

Sources & evidence

ORD record
ord-d49c3926d8314431a026b677fc453b36
Source dataset
uspto-grants-1977_06
Patent number
US04031127

Reaction notes

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