Citric Acid → HCID 19813042, compound

HRID 466964Notes

Reaction equation

HRID 466964 reaction equation
[NH:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[NH:4][C:3](=[O:13])[CH2:2]1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:4]1[C:5](=[O:12])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:1][CH2:2][C:3]1=[O:13]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 19024281HCID 19024281, compound

Product 1

HCID 19813042HCID 19813042, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide (DMF) was dissolved 100 mg of 2,3,4,5-tetrahydro-1,4-benzodiazepine-3,5-dione and the solution then ice-cooled. Then, to the resulting solution were added 0.116 ml (1.5 equivalent) of 1,5-dibromopentane and 27.3 mg (1.2 equivalent) of a 60% sodium hydride oil dispersion and the mixture was stirred for 2 hours with ice-cooling. The reaction solution was poured into ice-cooled water containing citric acid, made alkaline with sodium hydrogen carbonate, and extracted with ethyl acetate. The ethyl acetate phase was then washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The product was purified in the same manner as in Reference Example 1 to give 97.5 mg (yield: 52.8%) of the title compound.

Workup

  1. temperaturethe solution then ice-cooled
  2. temperaturecooling
  3. additionThe reaction solution was poured into ice-
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate phase was then washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe product was purified in the same manner as in Reference Example 1

Sources & evidence

ORD record
ord-69e22f3d838e418d95572570b8f4ab9f
Source dataset
uspto-grants-1992_10
Patent number
US05158947

Reaction notes

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