Phosgene → HCID 13557270, compound

HRID 1583479Notes

Reaction equation

HRID 1583479 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17](=[O:18])[C:16]([CH3:20])([CH3:19])[CH2:15][O:14]2)=[C:8]([Cl:21])[CH:7]=1>C1(C)C=CC=CC=1.O1CCCC1>[Cl:21][C:8]1[CH:7]=[C:6]([N:5]=[C:1]=[O:2])[CH:11]=[CH:10][C:9]=1[CH2:12][N:13]1[C:17](=[O:18])[C:16]([CH3:19])([CH3:20])[CH2:15][O:14]1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 13557219HCID 13557219, compound

Product 1

HCID 13557270HCID 13557270, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 7.9 grams (0.08 mole) of phosgene in toluene was added dropwise a solution of 5.0 grams (0.02 mole) of 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone in tetrahydrofuran. Upon completion of addition the reaction mixture was warmed to 80° C. where it stirred for 3 hours. The reaction mixture was concentrated under reduced pressure to give 5.6 grams of 2-(2-chloro-4-isocyanatophenyl)methyl-4,4-dimethyl-3-isoxazolidinone as a residual solid.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a740ad7d4284527b39aea485192ed0b
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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