2,5-Dichlorobenzoic acid → HCID 690459, compound

HRID 1766341Notes

Reaction equation

HRID 1766341 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:14].C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[C:13]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:2]=2[Cl:1])=[CH:17][CH:16]=1)(=[O:14])[CH3:12]

Participants

6

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 7468p-AminoacetophenoneHCID 8471Triethylamine

Product 1

HCID 690459HCID 690459, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Reaction of 2,5-dichlorobenzoic acid (300 mg, 1.50 mmol) in thionyl chloride (3.5 mL) then with 4-aminoacetophenone (85 mg, 0.63 mmol) in presence of triethylamine (90 μL, 0.65 mmol) in THF (6 mL) according to method B gave N-(4-Acetyl-phenyl)-2,5-dichloro-benzamide (150 mg, 0.48 mmol, 76% yield) as a orange powder after purification by crystallisation in DCM.

Sources & evidence

ORD record
ord-d57cb0399b104d92a2a4084ef8b21bd7
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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