2,5-Difluorobenzoyl chloride → HCID 69314684, compound

HRID 1168671Notes

Reaction equation

HRID 1168671 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-c920ac9e5b044096be150078f0afd166
Source dataset
uspto-grants-2003_09
Patent number
US06627624B1

Reaction notes

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