2,4-Dichlorobenzoyl chloride → HCID 67299243, compound

HRID 2193926Notes

Reaction equation

HRID 2193926 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:21][C:20]=2[C:30]([O:32][CH3:33])=[O:31])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:34][C:35]1[CH:43]=[C:42]([Cl:44])[CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38]>ClCCCl.CCOC(C)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][N:18]([C:37](=[O:38])[C:36]2[CH:40]=[CH:41][C:42]([Cl:44])=[CH:43][C:35]=2[Cl:34])[C:19]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[S:21][C:20]=2[C:30]([O:32][CH3:33])=[O:31])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 20775745HCID 20775745, compound

Product 1

HCID 67299243HCID 67299243, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[(2-Methoxycarbonyl-5-phenyl-thiophen-3-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester (133 mg, 0.28 mmol) was dissolved in 1,2-dichloroethane (2.8 mL) and was treated with 2,4-dichlorobenzoyl chloride (60 μL, 0.43 mmol). The solution was heated at reflux for 1 day. The solvent was then evaporated and the residue purified by silica gel column chromatography using hexanes:EtOAc as eluent to provide 4-{[(2,4-Dichloro-benzoyl)-(2-methoxycarbonyl-5-phenyl-thiophen-3-yl)-amino]-methyl}-piperidine-1-carboxylic acid benzyl ester (0.156 g, 85% yield).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 1 day
  3. customThe solvent was then evaporated
  4. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ef31e6c3bfb44066bea4f41fa9fcea8c
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

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