Triethylamine → HCID 66654500, compound

HRID 517737Notes

Reaction equation

HRID 517737 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([O:17][C:18]([F:21])([F:20])[F:19])[CH:10]=1.[C:22]([O:25][CH2:26][C:27](Cl)=[O:28])(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([O:25][CH2:26][C:27]([NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([O:17][C:18]([F:19])([F:20])[F:21])[CH:10]=1)=[O:28])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 230681124-amino-2-(trifluoromethoxy)benzonitrile2×

Product 1

HCID 66654500HCID 66654500, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (6.5 g, 64.2 mmol) was added to a stirred solution of 4-amino-2-[(trifluoromethyl)oxy]benzonitrile (Intermediate 51, 6.5 g, 32.2 mmol) in DCM (100 mL) at 0° C. and the mixture was stirred for 15 min. Chloro-2-oxoethyl acetate (5.2 g, 38.1 mmol) was added at 0° C. and stirring was continued for 4 hr at room temperature. The reaction mixture was diluted with DCM and washed with ice-water, saturated aq. NaHCO3 solution and brine solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (100-200 mesh silica gel), eluting with 30% EtOAc/pet ether to give the title compound (8.10 g).

Workup

  1. stirringstirring
  2. waitwas continued for 4 hr at room temperature
  3. washwashed with ice-water, saturated aq. NaHCO3 solution and brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product
  7. customThis was purified by column chromatography (100-200 mesh silica gel)
  8. washeluting with 30% EtOAc/pet ether

Sources & evidence

ORD record
ord-4c1b513b8d5942c2b49bcf8582102131
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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