Allyl bromide → Diethyl 4-(allylethylamino)benzylacetamidomalonate

HRID 1934316Notes

Reaction equation

HRID 1934316 reaction equation
[CH2:1]([NH:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][CH2:9][C:10]([NH:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])=[CH:6][CH:5]=1)[CH3:2].[CH2:26](Br)[CH:27]=[CH2:28].N12CCCC1=NCCC2>O1CCCC1>[CH2:28]([CH2:2][CH2:1][NH:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][CH2:9][C:10]([NH:12][CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11])=[CH:6][CH:5]=1)[CH:27]=[CH2:26]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 54294942Diethyl 4-ethylaminobenzylacetamidomalonate

Product 1

HCID 69892586Diethyl 4-(allylethylamino)benzylacetamidomalonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Working as in Example F, but starting with 8 g of diethyl 4-ethylaminobenzylacetamidomalonate, 4 ml of allyl bromide and 5.82 ml of 1,5-diazabicyclo-[4.3.0] non-5-ene in 50 ml of tetrahydrofuran, and after purification by flash chromatography (eluent: 90/10 CH2Cl2/EtOAc by volume), 5.6 g of a solid are obtained, which solid is recrystallized from 35 ml of cyclohexane. 5.43 g of diethyl 4-(allylethylamino)benzylacetamidomalonate are thus obtained in the form of a white solid melting at 86° C.

Workup

  1. customafter purification by flash chromatography (eluent: 90/10 CH2Cl2/EtOAc by volume), 5.6 g of a solid
  2. customare obtained
  3. customwhich solid is recrystallized from 35 ml of cyclohexane

Sources & evidence

ORD record
ord-528e95336e314263940a0b7e5edd89f5
Source dataset
uspto-grants-2002_05
Patent number
US06384014B1

Reaction notes

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