Hydrochloric Acid → HCID 19973109, compound

HRID 1451944Notes

Reaction equation

HRID 1451944 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:23])([CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1)[C:10]([F:16])([F:15])[C:11]([NH:13][NH2:14])=[O:12].C(N(CC)CC)C.[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1.Cl>ClCCl.O>[F:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH:14][NH:13][C:11](=[O:12])[C:10]([F:15])([F:16])[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])([OH:23])[CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[O:37])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 19973099HCID 19973099, compound

Product 1

HCID 19973109HCID 19973109, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 7 ml of dichloromethane was suspended 0.33 g of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyrohydrazide. To the suspension was added 0.12 g of triethylamine. Thereto was dropwise added 0.19 g of 4-fluorobenzoyl chloride at 5°-10° C. The resulting mixture was subjected to reaction at the same temperature for 1 hour. The reaction mixture was introduced into a mixed solvent consisting of 10 ml of dichloromethane and 10 ml of water. The resulting solution was adjusted to pH 1.0 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) to obtain 0.25 g of N'-(4-fluorobenzoyl)-3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyrohydrazide.

Workup

  1. customat 5°-10° C
  2. customThe resulting mixture was subjected to reaction at the same temperature for 1 hour
  3. additionThe reaction mixture was introduced into a mixed solvent
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThereafter, the solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography (eluant: chloroform)

Sources & evidence

ORD record
ord-383356bb7b5940b1a947bfe29cf6781d
Source dataset
uspto-grants-1997_02
Patent number
US05605921

Reaction notes

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