Chloroacetyl chloride → 2-chloro-N-(4-cyanophenyl)acetamide

HRID 925541Notes

Reaction equation

HRID 925541 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.[Cl:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)Cl>[Cl:17][CH2:18][C:19]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 133964-Aminobenzonitrile

Product 1

HCID 21680152-chloro-N-(4-cyanophenyl)acetamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
26 °C

Procedure

A mixture of 4-Amino benzonitrile (1.0 g, 0.0084 mol) and triethyl amine (1 ml, 0.010 mol) was taken in DCM (15 ml). Chloro acetyl chloride (0.67 ml, 0.0084 mol) was added slowly and stirred for 22 hours at 25-27° C. Solvent was removed and the residue was dissolved in ethyl acetate (20 ml), washed with water (1×15 ml) followed by brine (2×15 ml). The organic layer was dried over Na2SO4 and the solvent was removed to get pure 2-chloro-N-(4-cyano-phenyl)-acetamide (1.51 g, 92%).

Workup

  1. customSolvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washwashed with water (1×15 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-14b0d287f22342c3a097ca881321c7b7
Source dataset
uspto-grants-2016_03
Patent number
US09284316B2

Reaction notes

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