Methyl Isocyanate → Trans-3-{[(methylamino)carbonyl]oxy}-4-(4-chlorophenoxy)-N,N-dimethyl-1-pyrrolidinecarboxamide

HRID 1381222Notes

Reaction equation

HRID 1381222 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C@H:7]2[C@H:11]([OH:12])[CH2:10][N:9]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:8]2)=[CH:4][CH:3]=1.[CH3:20][N:21]=[C:22]=[O:23]>C(Cl)Cl>[CH3:20][NH:21][C:22]([O:12][C@H:11]1[C@H:7]([O:6][C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:8][N:9]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:10]1)=[O:23]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 13320214Trans-3-(4-chlorophenoxy)-4-hydroxy-N,N-dimethyl-1-pyrrolidinecarboxamide

Product 1

HCID 13320218Trans-3-{[(methylamino)carbonyl]oxy}-4-(4-chlorophenoxy)-N,N-dimethyl-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g. (0.003 mole) of trans-3-(4-chlorophenoxy)-4-hydroxy-N,N-dimethyl-1-pyrrolidine carboxamide and 1.0 g. (0.02 mole) of methylisocyanate in 20 ml. of methylene chloride was let stand at ambient temperature for 48 hr. The solution was concentrated to give an oil which crystallized upon standing. The solid was recrystallized from benzene-cyclohexane to yield 0.6 g. (50%) of white solid, m.p. 132°-134° C.

Workup

  1. concentrationThe solution was concentrated
  2. customto give an oil which
  3. customcrystallized
  4. customThe solid was recrystallized from benzene-cyclohexane
  5. customto yield 0.6 g

Sources & evidence

ORD record
ord-6e2cbb9b86304375a0c17051edfbab27
Source dataset
uspto-grants-1986_04
Patent number
US04585785

Reaction notes

Loading…