2,5-Dichlorobenzoic acid → HCID 21110330, compound

HRID 1766320Notes

Reaction equation

HRID 1766320 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.[NH2:12][C:13]1[CH:26]=[CH:25][C:16]([C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[C:17]([C:16]1[CH:15]=[CH:14][C:13]([NH:12][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:2]=2[Cl:1])=[CH:26][CH:25]=1)(=[O:18])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 143464-Aminobenzophenone

Product 1

HCID 21110330HCID 21110330, compoundYield 84.3%

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-aminobenzophenone (100 mg, 0.51 mmol) in presence of triethylamine (90 μL) in THF (6 mL) according to method B gave N-(4-benzoyl-phenyl)-2,5-dichloro-benzamide (160 mg, 0.43 mmol, 84% yield) as a off-white powder after purification by chromatography on silica gel (eluent:EtOAc/exane 1/9 to 3/7).

Sources & evidence

ORD record
ord-f1c5c74a643945c8855948800c172302
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

Loading…