Ethyl 2-methylacetoacetate → HCID 15716741, compound

HRID 1994227Notes

Reaction equation

HRID 1994227 reaction equation
[CH3:1][CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:11]([NH:18]/[C:8](/[CH3:10])=[C:2](/[CH3:1])\[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 7504Benzylamine2×

Product 1

HCID 15716741HCID 15716741, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2-methylacetoaceate (1-004-01) (115.34 g) and benzylamine (85.73 g) in toluene (1.6 L) was azeotropically dehydrated in an oil bath at 145° C. for 8 h under nitrogen atmosphere. Benzylamine was added to the reaction mixture and the reaction mixture was dehydrated again. After 6 h, the reaction mixture was distilled under atmospheric pressure to remove about 600 mL of the solvent, and evaporated under reduced pressure to give ethyl 3-benzylamino-2-methylcrotonate (1-004-02) (195.66 g).

Workup

  1. distillationthe reaction mixture was distilled under atmospheric pressure
  2. customto remove about 600 mL of the solvent
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d8dc94529ca44db48fe0ffa00904a3aa
Source dataset
uspto-grants-2010_01
Patent number
US07652141B2

Reaction notes

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