Acetoxyacetyl chloride → HCID 66653997, compound

HRID 517715Notes

Reaction equation

HRID 517715 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6].C(N(C(C)C)CC)(C)C.[C:23]([O:26][CH2:27][C:28](Cl)=[O:29])(=[O:25])[CH3:24]>ClCCl>[C:23]([O:26][CH2:27][C:28]([NH:1][C:2]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)=[O:29])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 26297Acetoxyacetyl chloride2×HCID 81531DiisopropylethylamineHCID 225022643-Amino-5-(trifluoromethyl)benzonitrile2×

Product 1

HCID 66653997HCID 66653997, compoundYield 109.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-amino-5-(trifluoromethyl)benzonitrile (Intermediate 28, 2.20 g, 11.82 mmol) and di-isopropylethylamine (2.27 mL, 13.0 mmol) in dichloromethane (40 mL) was cooled in an ice-water bath before the addition of 2-chloro-2-oxoethyl acetate (1.40 mL, 13.0 mmol) dropwise. The reaction was allowed to warm to room temperature and stirred for 4 hours. To the reaction was added 2-chloro-2-oxoethyl acetate (0.14 mL) and the reaction stirred at room temperature for a further 18 hours. The reaction was diluted with DCM (100 mL) and the solution washed with 2N HCl (75 mL) and NaHCO3 (75 mL), collected via a hydrophobic frit and the solvent removed to yield the title compound as an orange oil (3.7 g)

Workup

  1. stirringthe reaction stirred at room temperature for a further 18 hours
  2. washthe solution washed with 2N HCl (75 mL) and NaHCO3 (75 mL)
  3. customcollected via a hydrophobic frit
  4. customthe solvent removed

Sources & evidence

ORD record
ord-8e2c5c3d2bc4408386ec74cd26786ba6
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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