2-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine → 5-(4-Methylthiophenyl)-4-fluoromethyl-oxazolidin-2-one

HRID 2352353Notes

Reaction equation

HRID 2352353 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][C:12](=[O:14])[NH:11][CH:10]2[CH2:15]O)=[CH:5][CH:4]=1.ClC(F)C(N(CC)CC)(F)[F:20]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][C:12](=[O:14])[NH:11][CH:10]2[CH2:15][F:20])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amineHCID 136776195-(4-Methylthiophenyl)-4-hydroxymethyl-oxazolidin-2-one

Product 1

HCID 145977055-(4-Methylthiophenyl)-4-fluoromethyl-oxazolidin-2-oneYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 250 mg (1.0 mmole) of 5-(4-methylthiophenyl)-4-hydroxymethyl-oxazolidin-2-one in 30 ml of methylene chloride was added 0.21 ml (1.3 moles) of N-(2-chloro-1,1,2-trifluoroethyl)-diethylamine. The reaction mixture was heated in a teflon bomb at 110° C for 1.5 hours. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed twice with water, dried and concentrated. Chromatography on silica gel afforded 150 mg (0.62 mmole), 62% of 5-(4-methylthiophenyl)-4-fluoromethyl-oxazolidin-2-one.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe organic layer was washed twice with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aaee3c45389f4549844e9f9a8d89961a
Source dataset
uspto-grants-1989_10
Patent number
US04876352

Reaction notes

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