Hydrochloric Acid → HCID 19973119, compound

HRID 1451941Notes

Reaction equation

HRID 1451941 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:24])([CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)[C:10]([F:17])([F:16])[C:11](OCC)=[O:12].[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C(OCC)(=O)C.Cl>O>[Cl:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:11](=[O:12])[C:10]([F:16])([F:17])[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:24])[CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 8857Ethyl AcetateHCID 19973081HCID 19973081, compound

Product 1

HCID 19973119HCID 19973119, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 mg of ethyl 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyrate and 370 mg of 4-chloroaniline was subjected to reaction at 150°-160° C. for 5 hours. The reaction mixture was cooled to room temperature. Thereto were added 10 ml of ethyl acetate and 5 ml of water. The resulting solution was adjusted to pH 2.0 with 6N hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: toluene/ethyl acetate=1/1) to obtain 30 mg of N-(4-chlorophenyl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide.

Workup

  1. customwas subjected to reaction at 150°-160° C. for 5 hours
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThereafter, the solvent was removed by distillation under reduced pressure
  6. customThe residue obtained
  7. customwas purified by a column chromatography (eluant: toluene/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-d0a3d69e5ec540ca8db7919d1a0e63e9
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

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