2-Chlorobenzoxazole → HCID 13090853, compound

HRID 358184Notes

Reaction equation

HRID 358184 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][N:4]([CH3:9])[C:5](=[O:8])[CH2:6][OH:7].[OH-].[K+].Cl[C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1>C(#N)C>[F:1][C:2]([F:10])([F:11])[CH2:3][N:4]([CH3:9])[C:5](=[O:8])[CH2:6][O:7][C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 14797Potassium HydroxideHCID 13090851N-(2,2,2-trifluoroethyl)-N-methyl-hydroxyacetic acid amide

Product 1

HCID 13090853HCID 13090853, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

17.1 g (0.1 mol) of N-(2,2,2-trifluoroethyl)-N-methyl-hydroxyacetic acid amide and 7 g of potassium hydroxide powder were initially introduced into 100 ml of acetonitrile at 20° C., and 15.3 g (0.1 mol) of 2-chlorobenzoxazole were added at a temperature between 20° and 40° C. The reaction mixture was stirred at 40° C. for one hour and at 20° C. for a further 15 hours and was concentrated and the concentrate was shaken with toluene and water. The organic phase was washed with dilute sodium hydroxide solution, washed until neutral, dried and filtered. The solvent was carefully distilled off from the filtrate under reduced pressure. 15 g (52% of theory) of N-(2,2,2-trifluoroethyl)-N-methyl-benzoxazol-2-yl-oxy-acetic acid amide of melting point 92° C. were obtained as the residue.

Workup

  1. concentrationwas concentrated
  2. stirringthe concentrate was shaken with toluene and water
  3. washThe organic phase was washed with dilute sodium hydroxide solution
  4. washwashed until neutral,
  5. customdried
  6. filtrationfiltered
  7. distillationThe solvent was carefully distilled off from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-1a97c3c698a64f23bf2f33a17833901d
Source dataset
uspto-grants-1984_08
Patent number
US04465504

Reaction notes

Loading…