Hydrochloric Acid → 1-Cyano-2-hydroxy-1-(4-trifluoromethylphenyl)aminothiocarbonylpropene

HRID 962802Notes

Reaction equation

HRID 962802 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[S:8].N12CCCN=C1CCCCC2.Cl>C(O)C>[C:4]([C:3]([C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=1)=[S:8])=[C:2]([OH:6])[CH3:1])#[N:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 158588075-Methyl-4-(4-trifluoromethylphenyl)aminothiocarbonylisoxazole

Product 1

HCID 1363959891-Cyano-2-hydroxy-1-(4-trifluoromethylphenyl)aminothiocarbonylpropeneYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.0 grams of 5-methyl-4-(4-trifluoromethylphenyl)aminothiocarbonylisoxazole and 5 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene in 50 ml of ethanol was heated at 80° C. for 8 hours. The reaction mixture was cooled to room temperature and acidified with 6N hydrochloric acid solution until pH 2. The mixture was then cooled in an ice-water bath for 30 minutes and the solid was filtered, washed with a chilled solution of ethanol and water (2:1) and dried by suction to provide 5.0 grams of 1-cyano-2-hydroxy-1-(4-trifluoromethylphenyl)aminothiocarbonylpropene.

Workup

  1. temperatureThe mixture was then cooled in an ice-water bath for 30 minutes
  2. filtrationthe solid was filtered
  3. washwashed with a chilled solution of ethanol and water (2:1)
  4. customdried by suction

Sources & evidence

ORD record
ord-eb7d09cf125047bfbaa1952b846d81e9
Source dataset
uspto-grants-1998_06
Patent number
US05760066

Reaction notes

Loading…