Acetic Anhydride → 5-(Acetylamino)-2,4-dichlorobenzoic acid

HRID 2283213Notes

Reaction equation

HRID 2283213 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[C:15]([NH2:19])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]>CC(O)=O>[C:1]([NH:19][C:15]1[C:16]([Cl:18])=[CH:17][C:9]([Cl:8])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 52002455-amino-2,4-dichlorobenzoic acid

Product 1

HCID 2833165-(Acetylamino)-2,4-dichlorobenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (27 mL) was added to 2,4-dichloro-5-aminobenzoic Acid 1-3 (8.0 g, 0.041 mol) in glacial AcOH (150 mL). The solution was stirred at room temperature for 30 min and concentrated to yield the desired acetamide 1-4 as a white solid (9.6 g, 96%). 1H NMR (400 MHz, CD3OD) δ2.19 (s, 3H), 7.62 (s, 1H), 8.32 (s, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-e80f96cc675c4aa2b76c3bea0434b825
Source dataset
uspto-grants-2015_09
Patent number
US09145375B2

Reaction notes

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