Diethyl bromomalonate → diethyl N-benzyl-N-(2,4-dimethoxybenzyl)-amino-malonate

HRID 1388873Notes

Reaction equation

HRID 1388873 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>>[CH2:1]([N:8]([CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 69637Diethyl bromomalonateHCID 784822Benzyl-(2,4-dimethoxy-benzyl)-amine

Product 1

HCID 13422977diethyl N-benzyl-N-(2,4-dimethoxybenzyl)-amino-malonateYield 81%

Procedure

The compound obtained in the step (1a), is converted into the corresponding base and 175 g (0.68 moles) of benzyl (2,4-dimethoxybenzyl)-amine obtained are stirred with 89.6 g (0.38 moles, 64 ml) of diethyl bromomalonate at room temperature until the reaction mixture solidifies. The solidified mixture is triturated with about one liter of ether and the crystalline precipitate is filtered off. (In this way the excess of the starting amine can be recovered as the hydrobromide with a yield of 95%). The filtrate is evaporated and the residual oil is triturated with ethanol. 114.5 g (81%) of diethyl N-benzyl-N-(2,4-dimethoxybenzyl)-amino-malonate are obtained, melting at 62° to 63° C. after crystallization from ethanol.

Workup

  1. customThe compound obtained in the step (1a)
  2. customobtained
  3. customThe solidified mixture is triturated with about one liter of ether
  4. filtrationthe crystalline precipitate is filtered off
  5. custom(In this way the excess of the starting amine can be recovered as the hydrobromide with a yield of 95%)
  6. customThe filtrate is evaporated
  7. customthe residual oil is triturated with ethanol

Sources & evidence

ORD record
ord-0611d698c1a14f70934c54682dfee80e
Source dataset
uspto-grants-1984_02
Patent number
US04434099

Reaction notes

Loading…