2,5-Dichlorobenzoic acid → HCID 21110281, compound

HRID 1766312Notes

Reaction equation

HRID 1766312 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:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16]2.C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16]2)=[O:6]

Participants

6

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 3128905-amino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 21110281HCID 21110281, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Reaction of 2,5dichlorobenzoic acid (287 mg, 1.50 mmol) in thionyl chloride (3.5 mL) then with 5-amino-indan-1-one (74 mg, 0.50 mmol) in presence of triethylamine (0.5 mL) in THF (6 mL) according to method B gave 2,5-dichloro-N-(1-oxo-indan-5-yl)-benzamide (33 mg, 0.09 mmol, 35% yield) as a green powder after purification by chromatography on silica gel (eluent: DCM).

Sources & evidence

ORD record
ord-e654edc357d64254bc2220293983b61d
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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