Methyl Isocyanate → HCID 13557220, compound

HRID 1583478Notes

Reaction equation

HRID 1583478 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][O:10]2)=[C:4]([Cl:17])[CH:3]=1.[CH3:18][N:19]=[C:20]=[O:21]>C(Cl)(Cl)Cl>[Cl:17][C:4]1[CH:3]=[C:2]([NH:1][C:20]([NH:19][CH3:18])=[O:21])[CH:7]=[CH:6][C:5]=1[CH2:8][N:9]1[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 13557219HCID 13557219, compound

Product 1

HCID 13557220HCID 13557220, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1.4 grams (0.06 mole) of 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in 25 ml of chloroform, under an argon atmosphere, was added dropwise 5 ml of methyl isocyanate. Upon completion of addition the reaction mixture stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under reduced pressure to a residual solid. The solid was recrystallized from ethanol to give 1.4 grams of 2-[2-chloro-4-(methylaminocarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 227°-229° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a residual solid
  3. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-1549385028cd4e8c93cb9b0460921387
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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