Bromocyclopentane → HCID 18971741, compound

HRID 2395410Notes

Reaction equation

HRID 2395410 reaction equation
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.O[C:8]1[CH:9]=[C:10]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[H-].[Na+]>CN(C)C=O>[CH:1]1([C:12]2[CH:11]=[C:10]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]([O:27][CH3:28])=[O:26])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:9]=[CH:8][C:13]=2[O:14][CH3:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 18971812HCID 18971812, compound

Product 1

HCID 18971741HCID 18971741, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (800 mg, 5.3 mmoles) cyclopentyl bromide, (1.6 g, 5.3 mmoles) methyl 1-(3-hydroxy-4-methoxyphenyl)-1H-benzimidazole-5-carboxylate and 251 mg of 50% sodium hydride in 10 ml of dimethylformamide was stirred at 100° C. for 30 minutes. The reaction was cooled, poured onto H2O and extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated to give 2 g of crude product. Purification on silica gel with CH2Cl2 gave 1.1 g of methyl 1-(3-cyclopentyl-4-methoxyphenyl)-1H-benzimidazole-5-carboxylate. M.P.: 129°-131°.

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured onto H2O
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried
  5. customevaporated
  6. customto give 2 g of crude product
  7. customPurification on silica gel with CH2Cl2

Sources & evidence

ORD record
ord-d59e0e268fcd4f3c8fd563b622a9bc52
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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