Methyl Isocyanate → Trans-3-(4-chlorophenoxy)-4-hydroxy-N-methyl-1-pyrrolidinecarboxamide Hemihydrate

HRID 1262597Notes

Reaction equation

HRID 1262597 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:11][NH:10][CH2:9][CH:8]2[OH:12])=[CH:4][CH:3]=1.[CH3:15][N:16]=[C:17]=[O:18]>C(Cl)Cl>[OH2:6].[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[C@H:8]([OH:12])[CH2:9][N:10]([C:17]([NH:16][CH3:15])=[O:18])[CH2:11]2)=[CH:4][CH:3]=1.[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[C@H:8]([OH:12])[CH2:9][N:10]([C:17]([NH:16][CH3:15])=[O:18])[CH2:11]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 13320209HCID 13320209, compound

Product 1

HCID 131713517Trans-3-(4-chlorophenoxy)-4-hydroxy-N-methyl-1-pyrrolidinecarboxamide Hemihydrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.9 g. of 4-(4-chlorophenoxy)-3-pyrrolidinol in 50 ml. of methylene chloride was cooled to 0° C. and 0.24 g. of methyl isocyanate in 5 ml. of methylene chloride was added dropwise over the period of 10 min. Cooling was discontinued and stirring was continued for 1 hr. Solvent was then removed and the residue was crystallized from dimethylsulfoxide-water; m.p. 95 0°-98.5° C.

Workup

  1. temperatureCooling
  2. customSolvent was then removed
  3. customthe residue was crystallized from dimethylsulfoxide-water
  4. customm.p. 95 0°-98.5° C.

Sources & evidence

ORD record
ord-69dcbf240ea1450f8f9cfb9913fb43fd
Source dataset
uspto-grants-1984_06
Patent number
US04452809

Reaction notes

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