Dibutylamine → HCID 19861849, compound

HRID 1165423Notes

Reaction equation

HRID 1165423 reaction equation
[C:1]([CH2:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[O:12][CH2:11]2)=[CH:6][CH:5]=1)#[N:2].[CH2:15]([NH:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>CO>[C:1]([CH2:3][C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]([OH:12])[CH2:11][N:19]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:6][CH:5]=1)#[N:2]

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 49623844-(2-Oxiranylmethoxy)benzeneacetonitrile

Product 1

HCID 19861849HCID 19861849, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30 g. of 3-(4-cyanomethylphenoxy)propylene oxide were mixed with 133.5 ml dibutylamine and 300 ml methanol and stirred at room temperature for 20 hours. The mixture was concentrated in a rotary evaporator and the residue was taken up in 225 ml of 1 N hydrochloric acid. The acidic solution was extracted with a total of 300 ml of dichloromethane. The dichloromethane phase was discarded. The aqueous phase was mixed with about 70 ml of 4 N caustic soda solution and extracted by shaking with 200 ml dichloromethane. The dichloromethane phase was dried over sodium sulfate. The desiccant was filtered off and the dichloromethane was drawn off with a rotary evaporator.

Workup

  1. concentrationThe mixture was concentrated in a rotary evaporator
  2. extractionThe acidic solution was extracted with a total of 300 ml of dichloromethane
  3. additionThe aqueous phase was mixed with about 70 ml of 4 N caustic soda solution
  4. extractionextracted
  5. stirringby shaking with 200 ml dichloromethane
  6. dry with materialThe dichloromethane phase was dried over sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. customthe dichloromethane was drawn off with a rotary evaporator

Sources & evidence

ORD record
ord-5a0369a3615a491d8652ad8015c89595
Source dataset
uspto-grants-1990_03
Patent number
US04910203

Reaction notes

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