Diethyl Ether → 2(3H)-Benzoxazolone

HRID 2412402Notes

Reaction equation

HRID 2412402 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1C=C[CH:11]=[CH:10][C:9]=1O.C(OCC)C>N1C=CC=CC=1>[O:4]1[C:5]2[CH:6]=[CH:11][CH:10]=[CH:9][C:8]=2[NH:7][C:2]1=[O:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58012-AminophenolHCID 10928Ethyl chloroformate

Product 1

HCID 60432(3H)-Benzoxazolone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

38.4 cc (0.4 mol) of ethyl chloroformate are added, at a temperature between 0° and 10° C., to a solution of 38.4 g (0.35 mol) of o-aminophenol in 150 cc of pyridine. When the addition has ended, the reaction mixture is stirred for a further 2 hours and then poured into 1.5 liters of diethyl ether. The precipitate is filtered off. The ether in the filtrate is evaporated off on a rotary evaporator. The residue is heated to 180° C. in order to distill off the pyridine. After cooling, the residue is recrystallized from ethyl acetate. The melting point of the obtained compound is 136° C.

Workup

  1. additionWhen the addition
  2. filtrationThe precipitate is filtered off
  3. customThe ether in the filtrate is evaporated off on a rotary evaporator
  4. distillationto distill off the pyridine
  5. temperatureAfter cooling
  6. customthe residue is recrystallized from ethyl acetate
  7. customis 136° C.

Sources & evidence

ORD record
ord-0d594b775ad04cd89a6ba327c71a63e7
Source dataset
uspto-grants-1985_01
Patent number
US04492709

Reaction notes

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