Hydroxylamine → 2H-1,2-Benzoxazin-3(4H)-one

HRID 1377207Notes

Reaction equation

HRID 1377207 reaction equation
[NH2:1][OH:2].C(N(CC)CC)C.[C:10](Cl)(Cl)=[O:11].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[O:2]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:20][C:10](=[O:11])[NH:1]1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 1140TolueneHCID 6371Phosgene2×HCID 8471Triethylamine

Product 1

HCID 199374482H-1,2-Benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

The amino-alcohol was dissolved in THF (15 ml) and cooled to -10° C. under N2. To the mixture was added triethylamine (5.4 ml) and phosgene in toluene (4.6 ml). The addition of phosgene caused an exotherm which was maintained below 20° C. by the rate of addition. The progress of the reaction was monitored by HPLC and was typically complete in 15 minutes.

Workup

  1. temperaturewas maintained below 20° C. by the rate of addition

Sources & evidence

ORD record
ord-15e803b21d5941ac90e181fdaca2ca3b
Source dataset
uspto-grants-1997_09
Patent number
US05663467

Reaction notes

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