Methyl Isocyanate → N-Methyl 3-phenoxy-1-azetidinecarboxamide

HRID 903129Notes

Reaction equation

HRID 903129 reaction equation
CS([O-])(=O)=O.[O:6]([CH:13]1[CH2:16][NH:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].[CH3:19][N:20]=[C:21]=[O:22]>C1C=CC=CC=1>[CH3:19][NH:20][C:21]([N:15]1[CH2:16][CH:13]([O:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14]1)=[O:22]

Participants

6

Reactant 4

HCID 12228Methyl IsocyanateHCID 14798Sodium HydroxideHCID 85257MethanesulfonateHCID 128125013-Phenoxyazetidine

Product 1

HCID 13420164N-Methyl 3-phenoxy-1-azetidinecarboxamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The methanesulfonate of 3-phenoxyazetidine (10.5 g., 0.043 mole) was partitioned between 50 ml of benzene and 25 ml. of dilute sodium hydroxide. The benzene layer was dried over calcium sulfate and filtered. The filtrate was treated with 2.6 g. (0.043 mole) of methylisocyanate and the solution was stirred at room temperature for 18 hours. The resulting mixture was concentrated at reduced pressure and the residue was crystallized from a mixture of ethyl acetate-isopropyl ether to give 1.2 g. (14%) of product (m.p. 139°-141° C.).

Workup

  1. dry with materialThe benzene layer was dried over calcium sulfate
  2. filtrationfiltered
  3. additionThe filtrate was treated with 2.6 g
  4. concentrationThe resulting mixture was concentrated at reduced pressure
  5. customthe residue was crystallized from a mixture of ethyl acetate-isopropyl ether
  6. customto give 1.2 g

Sources & evidence

ORD record
ord-2ea87a6f475d4ea68b6f25720e31af84
Source dataset
uspto-grants-1980_10
Patent number
US04226861

Reaction notes

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