Water → HCID 178500781, compound

HRID 654993Notes

Reaction equation

HRID 654993 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=O)=[O:4].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.[CH2:22]=[C:23]=[O:24]>C1(C)C=CC=CC=1>[C:23]([C:5](=[C:6]([NH:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:3]([O:2][CH3:1])=[O:4])(=[O:24])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 10038KeteneHCID 74591Dimethyl 3-oxoglutarate

Product 1

HCID 178500781HCID 178500781, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dimethyl acetonedicarboxylate (50 g; 0.29 mmole) was dissolved in toluene (150 ml), and benzylamine (32.2 g; 0.3 mmole) was added thereto. The resultant mixture was heated under reflux for 30 minutes while elimination of water and then cooled to room temperature. Gaseous ketene was introduced therein. The precipitated crystals were collected by filtration and recrystallized from ethanol to give dimethyl 2-acetyl-3-benzylamino-2-pentenedioate. M.P., 123.5°-124.0° C.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-273605dffc614db5b81b986b761c528d
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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