Hydrochloric Acid → HCID 69689612, compound

HRID 276028Notes

Reaction equation

HRID 276028 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:23](I)[CH2:24][CH2:25][CH3:26].Cl>CN(C)C=O.C(OCC)(=O)C>[CH2:23]([CH2:4][CH2:3][CH2:2][C:1]([NH:6][C:7]1[CH:8]=[C:9]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:5])[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 18315414HCID 18315414, compound

Product 1

HCID 69689612HCID 69689612, compoundYield 116%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.86 g of ethyl 3-butyrylamino-4-nitrobenzoate in 10 ml of N,N-dimethylformamide was added dropwise to a slurry of 0.428 g of 60% sodium hydride and 10 ml of N,N-dimethylformamide at room temperature, and the mixture was stirred at room temperature for 30 minutes. Subsequently, a solution of 1.97 g of n-butyl iodide in 10 ml of N,N-dimethylformamide was added dropwise thereto, and the mixture was heated at 50° C. for 13 hours. The reaction solution was poured into a mixed solution of 70 g of dilute hydrochloric acid and 70 g of ethyl acetate for extraction. The resulting organic layer was washed twice with water, dried, and then concentrated under reduced pressure to obtain 2.59 g of crude ethyl 3-(N-n-butylbutyrylamino)-4-nitrobenzoate. Then, 0.81 g of 1-n-butyl-6-ethoxycarbonyl-2-n-propylbenzimidazole (94) were formed in the same manner as in Example 24.

Workup

  1. temperaturethe mixture was heated at 50° C. for 13 hours
  2. washThe resulting organic layer was washed twice with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e384d39e19c1413b9804d914de5a0b8f
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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