Hydrochloric Acid → HCID 19973095, compound

HRID 2380318Notes

Reaction equation

HRID 2380318 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-1-yl)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-36a54a6d9391489a886811ec43d82eeb
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

Loading…