Acetyl chloride → HCID 85817530, compound

HRID 1749483Notes

Reaction equation

HRID 1749483 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[C:11](Cl)(=[O:13])[CH3:12]>>[C:9]([CH2:8][C:4]1[CH:3]=[C:2]([NH:1][C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][CH:5]=1)#[N:10]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 4847850(3-Amino-phenyl)-acetonitrile

Product 1

HCID 85817530HCID 85817530, compoundYield 85%

Procedure

To a mixture of (3-amino-phenyl)-acetonitrile (500 mg, 3.79 mmol) and TEA (498 mg, 4.93 mmol) was added acetyl chloride (387 mg, 4.93 mmol) slowly at 0° C. The resulting mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with DCM twice. The combined organic layers were washed with aqueous ammonia chloride and brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound (558 mg, 3.20 mmol, 85% yield) as a pale-yellow solid. MS (ESI) m/z 175.1 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with DCM twice
  3. washThe combined organic layers were washed with aqueous ammonia chloride and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-040243ebf16b42bf9d8b9bd68a72fc35
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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