Acetyl chloride → 4-(n-Acetyl-cyclopentylamino)-3-methyl-iodobenzene

HRID 891967Notes

Reaction equation

HRID 891967 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][C:10]([I:13])=[CH:9][C:8]=2[CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[C:17](Cl)(=[O:19])[CH3:18]>O1CCCC1>[C:17]([N:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][C:8]=1[CH3:14])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 222410484-Cyclopentylamino-3-methyl-iodobenzene

Product 1

HCID 111752944-(n-Acetyl-cyclopentylamino)-3-methyl-iodobenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

0.5 g (1.7 mmol) of 4-cyclopentylamino-3-methyl-iodobenzene are dissolved in 20 ml tetrahydrofuran and after the addition of 81.3 mg (1.7 mmol) of sodium hydride (50% in oil) stirred for 1 hour at 40 ° C. After cooling to ambient temperature 0.1 ml (1.5 mmol) of acetyl chloride is added and the mixture is stirred overnight at ambient temperature. The solvent is distilled off and the residue distributed in water/ethyl acetate. The combined organic extracts are dried, concentrated by evaporation and chromatographed on silica gel, eluting with dichloromethane/ethanol 0 to 5%.

Workup

  1. additionis added
  2. stirringthe mixture is stirred overnight at ambient temperature
  3. distillationThe solvent is distilled off
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated by evaporation
  6. customchromatographed on silica gel
  7. washeluting with dichloromethane/ethanol 0 to 5%

Sources & evidence

ORD record
ord-3e84509824ca4332bb6b82f653a5e3a5
Source dataset
uspto-grants-2006_02
Patent number
US07005437B2

Reaction notes

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