Acetic Acid → 6-Bromo-1-cyclopentyl-2-methyl-1H-benzimidazole

HRID 2264363Notes

Reaction equation

HRID 2264363 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:15](OCC)(OCC)(OCC)[CH3:16].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:15]([CH3:16])[N:9]([CH:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66221Triethyl orthoacetateHCID 516892Sodium BicarbonateHCID 65343498HCID 65343498, compound

Product 1

HCID 674280416-Bromo-1-cyclopentyl-2-methyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat a mixture of 4-bromo-N2-cyclopentyl-benzene-1,2-diamine (10.6 g), triethyl orthoacetate (9.5 ml) and acetic acid (6.3 mL) at 100° C. for 2.5 h. Dilute with DCM and pour onto an aqueous saturated solution of sodium bicarbonate. Dry over sodium sulfate and remove the solvent under vacuum. Purify by silica gel column chromatography, eluting with DCM/ethanol-10% NH3 (0-3%) to afford 10.67 g of the title compound. MS (ES+): m/z=280 (M+H)+.

Workup

  1. temperatureHeat
  2. dry with materialDry over sodium sulfate
  3. customremove the solvent under vacuum
  4. customPurify by silica gel column chromatography
  5. washeluting with DCM/ethanol-10% NH3 (0-3%)

Sources & evidence

ORD record
ord-9fbd4e68e311494495f5ca37f688c39e
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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