2,4-Dichlorobenzoyl chloride → HCID 67299348, compound

HRID 1015622Notes

Reaction equation

HRID 1015622 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[NH:10][CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[CH:15][CH:16]=1)=[O:4].[Cl:33][C:34]1[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:35]=1[C:36](Cl)=[O:37]>ClCCl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][C:9]=1[N:10]([C:36](=[O:37])[C:35]1[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:34]=1[Cl:33])[CH2:11][C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:18]=2)=[CH:15][CH:16]=1)=[O:4]

Participants

5

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 20775770HCID 20775770, compound

Product 1

HCID 67299348HCID 67299348, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 5-Phenyl-3-{[5-(3-trifluoromethyl-phenyl)-furan-2-ylmethyl]-amino}-thiophene-2-carboxylic acid methylester (65 mg 0.142 mmol) in dichloromethane (3 ml) and saturated NaHCO3 solution (3 ml) was added a solution of 2,4-dichloro-benzoyl chloride (36 mg, 1.2 eq.) in dichloromethane (0.9 ml). The reaction mixture was stirred vigorously at room temperature for overnight. The organic phase was collected and the aqueous phase was extracted twice with methylene chloride (2×15 ml). The organic layers were combined, washed with water, brine and dried over anhydrous Na2SO4. Solvent was removed and residue was purified on silica gel using Hexane:EtOAc 9:1 as eluant to give the desired product in 78% yield (70 mg). The proton NMR indicated the presence of rotamers.

Workup

  1. customThe organic phase was collected
  2. extractionthe aqueous phase was extracted twice with methylene chloride (2×15 ml)
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customSolvent was removed
  6. customresidue was purified on silica gel

Sources & evidence

ORD record
ord-25d3093b2f104848a06c0d0f743997cf
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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