Triethylamine → 1-Methyl-beta-oxo-alpha-(2,6-dichlorophenylcarbamoyl)-2-pyrrolpropionitrile

HRID 127592

Reaction equation

HRID 127592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=[O:11].[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](=[O:22])[CH2:19][C:20]#[N:21].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](=[O:22])[CH:19]([C:10](=[O:11])[NH:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8])[C:20]#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 27771703-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile

Product 1

HCID 202854251-Methyl-beta-oxo-alpha-(2,6-dichlorophenylcarbamoyl)-2-pyrrolpropionitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the filtered solution of 4.4 g of 2,6-dichlorophenylisocyanate in 30 ml of toluene is added 2.5 g of 1-methyl-β-oxo-2-pyrrolpropionitrile and 2.1 g of triethylamine while stirring. The mixture is allowed to stand overnight at room temperature, whereupon it is filtered. The solids are washed with toluene and diethyl ether, taken up in 50 ml of methanol and the solution poured into the mixture of 6 ml of 5 N hydrochloric acid and 300 ml of water. The crystals formed are collected, washed with water, dried, triturated with ethanol, and recrystallized from methanol, to yield the 1-methyl-β-oxo-α-(2,6-dichlorophenylcarbamoyl)-2-pyrrolpropionitrile melting at 196°-199°.

Workup

  1. filtrationis filtered
  2. washThe solids are washed with toluene and diethyl ether
  3. additionthe solution poured into the mixture of 6 ml of 5 N hydrochloric acid and 300 ml of water
  4. customThe crystals formed
  5. customare collected
  6. washwashed with water
  7. customdried
  8. customtriturated with ethanol
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-aa5d06143fbb44aea1ef74dd2804a70f
Source dataset
uspto-grants-1981_03
Patent number
US04256759

Linked notes

Loading…