Ethanol → 2-(4-Chlorophenoxy)-N-(2-cyanoethyl)-2-methylpropanamide

HRID 66253Notes

Reaction equation

HRID 66253 reaction equation
C(O)C.[Na].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[C:13]([CH2:15][CH2:16][NH:17][C:18](=[O:23])[C:19](Br)([CH3:21])[CH3:20])#[N:14]>C1(C)C=CC=CC=1>[C:13]([CH2:15][CH2:16][NH:17][C:18](=[O:23])[C:19]([O:12][C:9]1[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=1)([CH3:21])[CH3:20])#[N:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 46844-ChlorophenolHCID 5360545SodiumHCID 54029148N-cyanoethyl alpha-bromo-isobutyramide

Product 1

HCID 713710612-(4-Chlorophenoxy)-N-(2-cyanoethyl)-2-methylpropanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 25 liter reactor fitted with cooling and stirring means there were poured 3 liters of ethanol, 60 g of sodium and 250 g of p-chlorophenol (1.944 mol). After stirring for 1 hour there were added 3 liters of toluene and the ethanol/toluene azeotrope was removed by distillation; 2 more liters of toluene were added and also 425 g of N-cyanoethyl α -bromo-isobutyramide, (1.944 mol).

Workup

  1. customInto a 25 liter reactor fitted
  2. temperaturewith cooling
  3. stirringAfter stirring for 1 hour there
  4. customthe ethanol/toluene azeotrope was removed by distillation
  5. addition2 more liters of toluene were added

Sources & evidence

ORD record
ord-39df1e5f7f404323818a74e6bd196d9e
Source dataset
uspto-grants-1978_12
Patent number
US04131617

Reaction notes

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