Ethanolamine → HCID 85844602, compound

HRID 749167Notes

Reaction equation

HRID 749167 reaction equation
[F:1][CH:2]([F:7])[C:3](OC)=[O:4].[CH2:8]([CH2:10][NH2:11])[OH:9].ClCCl>C(#N)C>[NH3:11].[F:7][CH:2]([F:1])[C:3]([NH:11][CH2:10][CH2:8][OH:9])=[O:4]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 6344DichloromethaneHCID 79012Methyl difluoroacetate

Product 2

HCID 222AmmoniaHCID 85844602HCID 85844602, compoundYield 195.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl difluoroacetate (5 g, 45 mmol) in acetonitrile (50 ml) was reacted with ethanolamine (2.66 ml, 45.4 mmol) at ambient temperature for 24 hours. The solvent was evaporated and the residual oil was purified by chromatography on silica gel, eluting with dichloromethane:methanol (96:4) then dichloromethane:methanolic ammonia (94:6) to yield 2,2-difluoro-N-(2-hydroxyethyl)acetamide (6.18 g, 98% yield):

Workup

  1. customThe solvent was evaporated
  2. customthe residual oil was purified by chromatography on silica gel
  3. washeluting with dichloromethane:methanol (96:4)

Sources & evidence

ORD record
ord-e2471430116d4b988ea6326d8d16cab5
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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