Ethanol → Ethyl 3-amino-2,2-difluoropropanoate--hydrogen chloride (1/1)

HRID 1485042Notes

Reaction equation

HRID 1485042 reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][CH2:7][C:8]([F:13])([F:12])[C:9]([OH:11])=[O:10].[CH2:14](O)[CH3:15]>>[ClH:3].[NH2:6][CH2:7][C:8]([F:13])([F:12])[C:9]([O:11][CH2:14][CH3:15])=[O:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 509988433-Amino-2,2-difluoropropanoic acid--hydrogen chloride (1/1)

Product 1

HCID 49853527Ethyl 3-amino-2,2-difluoropropanoate--hydrogen chloride (1/1)

Procedure

To ethanol (12.0 mL), thionyl chloride (0.587 mL) was added at 0° C. and the mixture was stirred at that temperature for 30 minutes. After adding 3-amino-2,2-difluoropropionic acid hydrochloride (950 mg) at 0° C., the mixture was refluxed for 4 hours. After being cooled to room temperature, the mixture was concentrated under reduced pressure. After adding ethyl acetate, the resulting precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to give the titled compound as a pale brown oil (920 mg).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionAfter adding ethyl acetate
  4. customthe resulting precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9275d41de3e245bd9225323d2b403247
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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