2,5-Dichlorobenzoic acid → HCID 21110282, compound

HRID 1766311Notes

Reaction equation

HRID 1766311 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.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][CH2:18][NH2:19].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:19][CH2:18][CH2:17][C:13]1[S:12][CH:16]=[CH:15][CH:14]=1)=[O:6]

Participants

6

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 116521Thiopheneethanamine

Product 1

HCID 21110282HCID 21110282, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Reaction of 2,5-dichlorobenzoic acid (164 mg, 0.85 mmol) in thionyl chloride (2 mL) then with 2-thiopheneethylamine (50 μL, 0.42 mmol) in presence of triethylamine (0.5 mL) in THF (3 mL) according to method B gave 2,5-dichloro-N-(2-thiophen-2-yl-ethyl)-benzamide (83 mg, 0.28 mmol, 66% yield) as a off-white powder after purification on silica gel (eluent: EtOAc/hexane 5/95 to 20/80).

Sources & evidence

ORD record
ord-070f412b02d64efea31df94f83a165f5
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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