Imidazole → benzyl (1H-imidazol-yl)hexanoate

HRID 1583417Notes

Reaction equation

HRID 1583417 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>CN(C)C=O>[N:3]1([CH:13]([CH2:12][CH2:11][CH2:10][CH3:9])[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 562258Benzyl 6-bromohexanoate

Product 1

HCID 86740497benzyl (1H-imidazol-yl)hexanoateYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a suspension of 9.74 g of 57% sodium hydride in 100 ml of dimethylformamide was added a solution of 15.0 g of imidazole in 500 ml of dimethylformamide at a temperature of 15°-25° C. The resulting mixture was heated to 60° C. for 1 hour, was cooled to room temperature and 62.8 g of benzyl 6-bromohexanoate was added. The mixture was heated to 60° C. for two hours, allowed to stand overnight at room temperature, and was evaporated. The residue was taken up in aqueous hydrochloric acid, washed with ether, made basic with sodium hydroxide and extracted with dichloromethane. The combined organic layers were dried, evaporated and distilled to yield 45.1 g (75%) of benzyl (1H-imidazol-yl)hexanoate.

Workup

  1. temperaturewas cooled to room temperature
  2. temperatureThe mixture was heated to 60° C. for two hours
  3. customwas evaporated
  4. washwashed with ether
  5. extractionextracted with dichloromethane
  6. customThe combined organic layers were dried
  7. customevaporated
  8. distillationdistilled

Sources & evidence

ORD record
ord-3488146e950b40eab37001aef354a9d9
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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