Hydrochloric Acid → HCID 20292076, compound

HRID 1389200Notes

Reaction equation

HRID 1389200 reaction equation
[CH2:1]([N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])[CH2:2][CH2:3][CH3:4].[C:11](Cl)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[OH-:21].[Na+]>O>[C:11]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:9][CH2:8][CH2:7][C:6]([OH:10])=[O:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 189842-Pyrrolidinone, 1-butyl-

Product 1

HCID 20292076HCID 20292076, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.5 g of n-butylpyrrolidone is heated for 20 hours under reflux in a mixture of 15 g of sodium hydroxide in 100 ml of water. Into the solution (which is cooled to 0° and vigorously agitated) there is slowly introduced (drop by drop) 23.1 g of benzoyl chloride, which is then stirred for a further 5 hours; while further cooling, 5 N hydrochloric acid is added until the reaction mixture becomes acid. The precipitated deposit, which still contains benzoic acid, is separated and recrystallized several times from ligroin to obtain 13.6 g (47% of theory) of N-benzoyl-4-(n-butyl)aminobutyric acid (M.P. 62° to 64°).

Workup

  1. temperatureInto the solution (which is cooled to 0°
  2. stirringis then stirred for a further 5 hours
  3. customThe precipitated deposit, which still contains benzoic acid, is separated
  4. customrecrystallized several times from ligroin

Sources & evidence

ORD record
ord-d9ae3cda06454ce68eac55e9ed438580
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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