Hydrochloric Acid → HCID 19973095, compound

HRID 1451945Notes

Reaction equation

HRID 1451945 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:30])[C:11]([F:29])([F:28])[C:12]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])([OH:19])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.O.C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:30])[C:11]([F:29])([F:28])[C:12]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[F:27])([OH:19])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 19973086HCID 19973086, compound

Product 1

HCID 19973095HCID 19973095, compoundYield 38.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

In 4 ml of methylene chloride was dissolved 80 mg of N-(2-methoxyphenyl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide. To the resulting solution were added 120 mg of ethanethiol and 130 mg of aluminum chloride at -5° to 0° C. The resulting mixture was subjected to reaction at 20°-25° C. for 20 hours. Then, the reaction mixture was introduced into a mixed solvent consisting of 10 ml of chloroform 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 thus obtained was purified by a column chromatography (eluant: chloroform/methanol=20/1) to obtain 30 mg of N-(2-hydroxyphenyl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1yl)butanamide.

Workup

  1. customThe resulting mixture was subjected to reaction at 20°-25° C. for 20 hours
  2. additionThen, the reaction mixture was introduced into a mixed solvent
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThereafter, the solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by a column chromatography (eluant: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-2b40bef924e54838a35c8d454418df50
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

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