Triethylamine → HCID 2107996, compound

HRID 517696Notes

Reaction equation

HRID 517696 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17]([O:20][CH2:21][C:22](Cl)=[O:23])(=[O:19])[CH3:18]>ClCCl>[C:17]([O:20][CH2:21][C:22]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)=[O:23])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 133964-AminobenzonitrileHCID 26297Acetoxyacetyl chloride

Product 1

HCID 2107996HCID 2107996, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-aminobenzonitrile (5 g, 42.3 mmol) and triethylamine (7.08 mL, 50.8 mmol) in dichloromethane (DCM) (40 mL) was cooled in an ice-water bath before the dropwise addition of 2-chloro-2-oxoethyl acetate (5.46 mL, 50.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction mixture was diluted with DCM (50 mL) and the resulting solution washed with 2N HCl (50 mL). On mixing, precipitation occurred and the solid collected was filtered and dried under vacuum at 40° C. for 4 hours to yield a pale brown solid. The solid was dissolved in DCM (150 mL) and washed with 2N HCl (50 mL). The organic layer was collected via a hydrophobic frit and the solvent removed to yield the title compound as a cream solid (4.48 g).

Workup

  1. washthe resulting solution washed with 2N HCl (50 mL)
  2. additionOn mixing
  3. customprecipitation
  4. customthe solid collected
  5. filtrationwas filtered
  6. customdried under vacuum at 40° C. for 4 hours
  7. customto yield a pale brown solid
  8. washwashed with 2N HCl (50 mL)
  9. customThe organic layer was collected via a hydrophobic frit
  10. customthe solvent removed

Sources & evidence

ORD record
ord-64621932199e42d99782fd51d726da2a
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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