2,5-Difluorobenzoyl chloride → HCID 69314684, compound

HRID 1393902Notes

Reaction equation

HRID 1393902 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:12]([NH:15][CH2:16][C:17]1[N:21]([CH2:22][CH2:23][CH3:24])[C:20]2[CH:25]=[CH:26][C:27]([CH2:29][O:30][Si:31]([CH3:37])([CH3:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][C:19]=2[N:18]=1)[CH2:13][CH3:14]>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([N:15]([CH2:12][CH2:13][CH3:14])[CH2:16][C:17]1[N:21]([CH2:22][CH2:23][CH3:24])[C:20]2[CH:25]=[CH:26][C:27]([CH2:29][O:30][Si:31]([CH3:36])([CH3:37])[C:32]([CH3:34])([CH3:33])[CH3:35])=[CH:28][C:19]=2[N:18]=1)=[O:5]

Participants

4

Reactant 2

HCID 5880822,5-Difluorobenzoyl chlorideHCID 22270286HCID 22270286, compound

Product 1

HCID 69314684HCID 69314684, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,5-difluorobenzoylchloride 1.5 eq is treated with 1.0 eq 1.25 g (3.3 mmole) of propyl({1-propyl-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]benzimidazol-2-yl}methyl)amine in dichloromethane at room temperature for 1 hr. The reaction is quenched with 1 N NaOH and partitioned between dichloromethane and water. The organic layer is dried over anhydrous Na2SO4 and the solvent removed in vacuo. The residue is chromatographed (SiO2) with ethyl acetate to afford 74% of (2,5-difluorophenyl)-N-propyl-N-({1-propyl-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]benzimidazol-2-yl}methyl)carboxamide.

Workup

  1. customThe reaction is quenched with 1 N NaOH
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layer is dried over anhydrous Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue is chromatographed (SiO2) with ethyl acetate

Sources & evidence

ORD record
ord-59c8af47e8be48acbe4eb4a2ebcf4ee8
Source dataset
uspto-grants-2008_03
Patent number
US07348326B2

Reaction notes

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