2-Chloroethyl isocyanate → 2-[[[[(2-Chloroethyl)amino]carbonyl]amino]methyl]-5-(phenylmethoxy)-2-(phenylmethyl)-4(1H)-pyridinone

HRID 1252606Notes

Reaction equation

HRID 1252606 reaction equation
[NH2:1][CH2:2][C:3]1[N:4](CC2C=CC=CC=2)[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.[Cl:25][CH2:26][CH2:27][N:28]=[C:29]=[O:30]>C(OCC)(=O)C>[Cl:25][CH2:26][CH2:27][NH:28][C:29]([NH:1][CH2:2][C:3]1([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:7](=[O:9])[C:6]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][NH:4]1)=[O:30]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 120385614(1H)-Pyridinone, 2-(aminomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-

Product 1

HCID 201403872-[[[[(2-Chloroethyl)amino]carbonyl]amino]methyl]-5-(phenylmethoxy)-2-(phenylmethyl)-4(1H)-pyridinoneYield 185.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 48.0 g (0.15 mol) of 2-(aminomethyl)-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone in 1.5 l of ethyl acetate was added 12.8 ml (0.15 mol) of 2-chloroethylisocyanate. The mixture was stirred overnight at room temperature, the product filtered off by suction, washed with ethyl acetate, and dried in vacuo, yielding 59.6 g of the title compound, melting point 130° C.

Workup

  1. filtrationthe product filtered off by suction
  2. washwashed with ethyl acetate
  3. customdried in vacuo

Sources & evidence

ORD record
ord-821b738d6c6d4d7d9260303e91a32432
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

Loading…