Acetic Anhydride → N-(2,3-dichlorophenyl)acetamide

HRID 1157398Notes

Reaction equation

HRID 1157398 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C1C=CC=CC=1>[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 118442,3-Dichloroaniline

Product 1

HCID 247148N-(2,3-dichlorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution 2.06 g (12.71 mmol) of 2,3-dichloroaniline (16-1) in 10 mL of benzene cooled in an ice bath was added drop wise a 10 mL benzene solution of 1.95 g (19.07 mmol) of acetic anhydride. The reaction mixture was then brought to reflux for 1 hour, cooled to room temperature and filtered off the desired product 16-2. MS (M+1): theoretical 203.0; measured 204.1. 1H NMR (CDCl3): 2.26 (s, 3H), 7.21 (m, 2H), 7.68 (m, 1H), 8.33 (m, 1H).

Workup

  1. temperatureto reflux for 1 hour
  2. filtrationfiltered off the desired product 16-2

Sources & evidence

ORD record
ord-2294da818b2442739b5aa9b1a87b1e46
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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