Sodium Bicarbonate → N-n-propyl-N-(2-ethoxycarbonylbenzyl)-4-ethoxycarbonylmethylaniline

HRID 904185Notes

Reaction equation

HRID 904185 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)[CH2:2][CH3:3].C(=O)([O-])O.[Na+].Br[CH2:23][C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]>O>[CH2:1]([N:4]([CH2:23][C:24]1[CH:34]=[CH:33][CH:32]=[CH:31][C:25]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11032082Ethyl 2-(bromomethyl)benzoateHCID 23333610N-n-propyl-4-ethoxycarbonylmethylaniline

Product 1

HCID 23333601N-n-propyl-N-(2-ethoxycarbonylbenzyl)-4-ethoxycarbonylmethylanilineYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-n-propyl-4-ethoxycarbonylmethylaniline (11.1 g, b.p. 131°-135°C./0.5 mmHg), sodium hydrogencarbonate (6.3 g), water (10 ml), and ethyl 2-bromomethylbenzoate (14.6 g) were treated in the same manner as described in Example 1 to obtain N-n-propyl-N-(2-ethoxycarbonylbenzyl)-4-ethoxycarbonylmethylaniline (16.5 g).

Sources & evidence

ORD record
ord-f2fe747f834641ae9a57cc1fc66d20f3
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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