Hydrochloric Acid → 2-(3-Isocyanatophenyl)-4H-3,1-benzoxazin-4-one

HRID 1589596Notes

Reaction equation

HRID 1589596 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[O:13][C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[C:20](Cl)(Cl)=[O:21]>ClC1C=CC=CC=1>[N:1]([C:2]1[CH:3]=[C:4]([C:8]2[O:13][C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1)=[C:20]=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 202453952-(3-Aminophenyl)-4H-3,1-benzoxazin-4-one

Product 1

HCID 202453802-(3-Isocyanatophenyl)-4H-3,1-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

40 Parts by weight of 2-(m-aminophenyl)-3,1-benzoxazin-4-one are suspended in 300 parts by volume of chlorobenzene and the suspension is treated with hydrogen chloride gas until saturated therewith, and then with phosgene gas for 4 hours at 110° C. The clear solution is concentrated under reduced pressure and the residue is then washed with ether and petroleum ether, giving 39 parts by weight of 2-(m-isocyanatophenyl)-3,1-benzoxazin-4-one of melting point 115°-121° C.

Workup

  1. concentrationThe clear solution is concentrated under reduced pressure
  2. washthe residue is then washed with ether and petroleum ether

Sources & evidence

ORD record
ord-66b1246e37e2472a9f1eccc033b62e8d
Source dataset
uspto-grants-1986_02
Patent number
USRE032087

Reaction notes

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