4-Chloro-3-trifluoromethylbenzoic acid hydrazide → HCID 178516245, compound

HRID 661417Notes

Reaction equation

HRID 661417 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=O)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].I.CS[C:19](=[NH:28])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[NH:28][C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[N:9][N:8]=2)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13]

Participants

4

Reactant 2

HCID 213117014-Chloro-3-trifluoromethylbenzoic acid hydrazideHCID 178504017HCID 178504017, compound

Product 1

HCID 178516245HCID 178516245, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-chloro-3-trifluoromethylbenzoic acid hydrazide (2.89 g, 12.1 mmol) and S-methyl N-(4-hydroxyphenyl)isothiourea hydroiodide (3.75 g, 12.1 mmol) were suspended in 40 mL of anhydrous pyridine. The reaction mixture was refluxed for 18 hours, during which time it changed color from yellow into dark-red. Then it was cooled down to ambient temperature and poured with stirring into 250 mL of ice-water. The aqueous solution was decanted and the oily residue was purified by silica gel chromatography using 1:1 mixture of ethyl acetate/hexane. Solvent was removed in vacuo to give the title product as a white solid (1.95 g). Yield 45.5%.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours, during which time it
  2. additionpoured
  3. customThe aqueous solution was decanted
  4. customthe oily residue was purified by silica gel chromatography
  5. addition1:1 mixture of ethyl acetate/hexane
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-a99d184d11c84f01b3d8631cd54af9c7
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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