p-Anisoyl chloride → HCID 2739532, compound

HRID 1766308Notes

Reaction equation

HRID 1766308 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH2:8].[C:9](Cl)(=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C1COCC1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][CH2:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[O:18])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 116521Thiopheneethanamine

Product 1

HCID 2739532HCID 2739532, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 2-thiopheneethylamine (50 μL, 0.42 mmol) in THF (2.5 mL) with p-anisoyl chloride(74 μL, 0.57 mmol) in presence of triethylamine (78 μL, 0.55 mmol) according to method A gave 4-methoxy-N-(2-thiophen-2-yl-ethyl)-benzamid (105 mg,0.40 mmol, 95% yield) as a white powder after purification by chromatography on silica gel (eluent: EtOAc/hexane 5/95 to 20/80).

Sources & evidence

ORD record
ord-3d8207fc73bd4cac9833fc6ae8dc7e23
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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