Phosgene → 1,4-Dihydro-2H-3,1-benzoxazin-2-one

HRID 1088791Notes

Reaction equation

HRID 1088791 reaction equation
[OH:1][CH2:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[C:17](Cl)(Cl)=[O:18].ClC(OC(Cl)(Cl)Cl)=O>O1CCCC1>[O:18]=[C:17]1[O:1][CH2:2][C:3]2[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=2[NH:5]1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 10426DiphosgeneHCID 214392-Aminobenzyl alcohol

Product 1

HCID 257861,4-Dihydro-2H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-hydroxymethylaniline (25 g), triethylamine (32 ml) and tetrahydrofuran (250 ml) was introduced phosgene generated from trichloromethyl chloroformate (12.2 ml) and active carbon at room temperature with stirring. After stirring for 1 hour at room temperature, the reaction mixture was filtered off and the filtrate was concentrated. The resulting residue was recrystallized from diethyl ether-n-hexane to give 4H-1,2-dihydro-2-oxo-[3,1]benzoxazine (22.3 g).

Workup

  1. stirringAfter stirring for 1 hour at room temperature
  2. filtrationthe reaction mixture was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was recrystallized from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-81193c6e07db4bf5abd99c9d96cdb676
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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