Water → Ethyl N-(2-buten-1-yl)-N-(2,2-dimethoxyethyl)-carbamate

HRID 981115Notes

Reaction equation

HRID 981115 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][NH:5][C:6](=[O:10])[O:7][CH2:8][CH3:9].[H-].[Na+].Br[CH2:16][CH:17]=[CH:18][CH3:19].O>C1(C)C=CC=CC=1>[CH2:16]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:11][CH3:12])[C:6](=[O:10])[O:7][CH2:8][CH3:9])[CH:17]=[CH:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1224142-Butene, 1-bromo-HCID 10921057Ethyl 2,2-dimethoxyethylcarbamate

Product 1

HCID 54206204Ethyl N-(2-buten-1-yl)-N-(2,2-dimethoxyethyl)-carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

89 g (0.5 mol) of ethyl N-(2,2-dimethoxyethyl)carbamate are added dropwise to 17.5 g (0.58 mol) of NaH (80% strength in paraffin oil) in 500 ml of absolute toluene at 80° C. The mixture is then stirred for one hour and 80 g (0.59 mol) of 1-bromo-2-butene are subsequently added dropwise at 80° C. The mixture is stirred at 80° C. overnight and cooled, the salts are dissolved with water and the aqueous phase is separated off and extracted with toluene. The toluene solutions are dried over K2CO3 and concentrated and the residue is distilled.

Workup

  1. stirringThe mixture is stirred at 80° C. overnight
  2. temperaturecooled
  3. customthe aqueous phase is separated off
  4. extractionextracted with toluene
  5. dry with materialThe toluene solutions are dried over K2CO3
  6. concentrationconcentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-c9e327700c2b49fb8d107b4fe1bd589d
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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