4-Chloro-1,2-diaminobenzene → N-(2-acetamido-4-chlorophenyl)acetamide

HRID 861449Notes

Reaction equation

HRID 861449 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].[C:17]([O-])(=[O:19])[CH3:18].[Na+]>Cl.O>[C:10]([NH:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:17](=[O:19])[CH3:18])(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 72634-Chloro-1,2-diaminobenzeneHCID 7918Acetic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 221796N-(2-acetamido-4-chlorophenyl)acetamideYield 21%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

28.4 g (0.2 mol) of 4-chloro-1,2-phenylenediamine were dissolved in 130 ml of 3 molar hydrochloric acid and diluted with 300 ml of water. 51 g (0.5 mol) of acetic anhydride were added dropwise and then the reaction mixture was stirred at room temperature for 30 minutes, 41 g (0.6 mol) of sodium acetate were added, and the mixture was extracted with ethyl acetate. Workup of the organic phase resulted in a yield of 21% of the product. Melting point 216° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-259cd193a984407cbc74f5d5a3aec0c0
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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