Triethylamine → HCID 86748274, compound

HRID 2380321Notes

Reaction equation

HRID 2380321 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10]([F:14])([F:13])[C:11]#[N:12].Cl.[NH2:23][OH:24].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10]([F:13])([F:14])[C:11](=[N:23][OH:24])[NH2:12]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 19973111HCID 19973111, compound

Product 1

HCID 86748274HCID 86748274, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

In 6 ml of chloroform was dissolved 300 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanenitrile. To the resulting solution were added 83 mg of hydroxylamine hydrochloride and 100 mg of triethylamine at 0°-5° C. The resulting mixture was subjected to reaction at 20°-25° C. for 3 hours. 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 9.0 with a saturated aqueous sodium hydrogencarbonate solution. 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 to obtain 330 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanamide oxime.

Workup

  1. customThe resulting mixture was subjected to reaction at 20°-25° C. for 3 hours
  2. additionThe 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

Sources & evidence

ORD record
ord-fcb3a748cf944fd9bfd5ddc49a71b826
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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