Butyronitrile, 3-amino- → HCID 53921112, compound

HRID 259606Notes

Reaction equation

HRID 259606 reaction equation
[CH3:1][O:2][C:3]([NH:5][CH:6]=[CH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]2[O:16][CH2:15]2)=[CH:10][CH:9]=1)=[O:4].[NH2:19][CH:20]([CH3:24])[CH2:21][C:22]#[N:23]>C(#N)C>[CH3:1][O:2][C:3]([NH:5][CH:6]=[CH:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]([OH:16])[CH2:15][NH:19][CH:20]([CH3:24])[CH2:21][C:22]#[N:23])=[CH:10][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 123366Butyronitrile, 3-amino-HCID 543618201-[p-(2-Methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxypropane

Product 1

HCID 53921112HCID 53921112, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3.0 g (0.012 mol) of 1-[p-(2-methoxycarbonylaminovinyl)-phenoxy]-2,3-epoxypropane are dissolved in 25 ml of acetonitrile and added dropwise to a boiling stirred solution of 0.96 g (0.011 mol) of β-aminobutyronitrile in 20 ml of acetonitrile. The mixture is stirred for 20 hours under reflux, the solvent is removed by distillation under reduced pressure and the oil which remains is partitioned between 150 ml of 0.1 N hydrochloric acid and 100 ml of ethyl acetate. The hydrochloric acid extract is separated off, rendered alkaline with sodium carbonate and extracted four times with 50 ml of ethyl acetate at a time. The organic phases are dried over sodium sulphate and evaporated under reduced pressure. The resulting oil solidifies on cooling to give crystals of 1-[p-(2-methoxycarbonylaminovinyl)-phenoxy]-2-hydroxy-3-(2-cyano-1-methylethyl-amino)-propane of melting point 122°-123° C.

Workup

  1. additionadded dropwise to a boiling
  2. temperatureunder reflux
  3. customthe solvent is removed by distillation under reduced pressure
  4. customthe oil which remains is partitioned between 150 ml of 0.1 N hydrochloric acid and 100 ml of ethyl acetate
  5. extractionThe hydrochloric acid extract
  6. customis separated off
  7. extractionextracted four times with 50 ml of ethyl acetate at a time
  8. dry with materialThe organic phases are dried over sodium sulphate
  9. customevaporated under reduced pressure
  10. temperatureon cooling

Sources & evidence

ORD record
ord-b1902f097d6745db88b517ac4df082f3
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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