Hydrochloric Acid → HCID 19973116, compound

HRID 2380306Notes

Reaction equation

HRID 2380306 reaction equation
Cl[CH2:2][C:3]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])([OH:12])[C:4]([F:11])([F:10])[C:5](OCC)=[O:6].[NH3:21].C(O)C.C(OCC)(=O)C.Cl>C(O)C.O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:3]1([O:12][CH2:2]1)[C:4]([F:11])([F:10])[C:5]([NH2:21])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 19973115HCID 19973115, compoundHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Product 1

HCID 19973116HCID 19973116, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 17 ml of ethanol was dissolved 1.7 g of ethyl 4-chloro-3-(2,4-dichlorophenyl)-2,2-difluoro-3-hydroxybutyrate. To the resulting solution was added 16.3 ml of a 3N ammonia-ethanol solution. The solution was subjected to reaction at 25°-30° C. for 24 hours. Then, the solvent was removed by distillation under reduced pressure. To the residue obtained were added 20 ml of ethyl acetate and 20 ml of water. The resulting mixture 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. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant: chloroform) to obtain 0.88 g of 3-(2,4-dichlorophenyl)-3,4-epoxy-2,2-difluorobutanamide.

Workup

  1. customThe solution was subjected to reaction at 25°-30° C. for 24 hours
  2. customThen, the solvent was removed by distillation under reduced pressure
  3. customTo the residue obtained
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe 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-4ea9498b9860405f8e2be0cc892a2260
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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