Ammonia → HCID 22115309, compound

HRID 1276358Notes

Reaction equation

HRID 1276358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6].[C:11]([O:20]C)(=O)[C:12]([CH2:14][C:15](OC)=O)=[CH2:13].[NH3:22].C[OH:24]>>[NH2:22][C:13]([CH:12]1[CH2:14][CH2:15][N:6]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:2]([Cl:1])[CH:3]=2)[C:11]1=[O:20])=[O:24]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 1608Benzenemethanamine, 3,4-dichloro-HCID 69240Dimethyl itaconate

Product 1

HCID 22115309HCID 22115309, compound

Procedure

Neat 3,4-dichlorobenzylamine (18 g, 114 mmol) was added to a solution of dimethyl itaconate (20 g, 114 mmol) in methanol (200 mL) at room temperature. The solution was stirred at for 48 h then concentrated in vacuo. The resulting solid was divided equally into two, one portion being treated with methanolic ammonia (7 M, 300 mL, 2.1 mol). The solution was vented with a needle and allowed to stand for 2 days. The slurry of solvent and product was concentrated further and filtered. The filter cake was washed with cold methanol to give pure 3-aminocarbonyl-1-(3,4-dichlorobenzyl)-pyrrolidin-2-one (18.5 g).

Workup

  1. concentrationthen concentrated in vacuo
  2. waitto stand for 2 days
  3. concentrationThe slurry of solvent and product was concentrated further
  4. filtrationfiltered
  5. washThe filter cake was washed with cold methanol

Sources & evidence

ORD record
ord-54dbc2b8aea048fe9bae188c76c13377
Source dataset
uspto-grants-2000_12
Patent number
US06166015

Reaction notes

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