Acrylonitrile → HCID 53679093, compound

HRID 1762586Notes

Reaction equation

HRID 1762586 reaction equation
C(N(CC)CC)C.[C:8](#[N:11])[CH:9]=[CH2:10].[CH2:12]([O:14][C:15](=[O:30])[CH2:16][CH2:17][NH:18][CH2:19][C:20]1[C:23]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=2[CH:21]=1)[CH3:13]>C(O)C>[CH2:12]([O:14][C:15](=[O:30])[CH2:16][CH2:17][N:18]([CH2:10][CH2:9][C:8]#[N:11])[CH2:19][C:20]1[C:23]2[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:22]=2[CH:21]=1)[CH3:13]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 54348879HCID 54348879, compound

Product 1

HCID 53679093HCID 53679093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.5 g (0.1 mol) of triethylamine and 5.84 g (0.11 mol) of acrylonitrile are added to 30.16 g (0.1 mol) of 3-(5-methoxybenzocyclobuten-1-ylmethylamino)-propionic acid ethyl ester in 250 ml of ethanol and the whole is stirred at room temperature for 15 hours. The reaction mixture is then concentrated under a water-jet vacuum, and the residue is taken up in diethyl ether and washed neutral with ice-water. The ethereal solution is dried over potassium carbonate, filtered and concentrated by evaporation; 3-{N-(2-cyanoethyl)-N-[(5-methoxybenzocyclobuten-1-yl)methyl]amino} propionic acid ethyl ester is obtained in the form of a yellow oil.

Workup

  1. concentrationThe reaction mixture is then concentrated under a water-jet vacuum
  2. washwashed neutral with ice-water
  3. dry with materialThe ethereal solution is dried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-8c8e39ecbc30475286d1633916d0f89e
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

Loading…