Hydrochloric Acid → 7-Acetyl-5-(benzyloxy)-1,3-benzoxazol-2(3H)-one

HRID 29815Notes

Reaction equation

[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[C:7]([OH:23])=[C:8]([C:20](=[O:22])[CH3:21])[CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1.Cl>N1C=CC=CC=1>[C:20]([C:8]1[C:7]2[O:23][C:1](=[O:2])[NH:5][C:6]=2[CH:11]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=1)(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 50 °C

Procedure

52 g (0.53 mol) phosgene are piped into a solution of 121 g (0.47 mol) 1-(3-amino-5-benzyloxy-2-hydroxy-phenyl)-ethanone in 800 mL pyridine at 20 to 40° C. The reaction mixture is heated to 50° C. for 2 hours, then poured onto ice and acidified with conc. hydrochloric acid. A reddish-brown solid is isolated which is repeatedly recrystallised from ethanol with the addition of activated charcoal.

Workup

additionpoured onto ice
customA reddish-brown solid is isolated which
customis repeatedly recrystallised from ethanol with the addition of activated charcoal

Sources & evidence

ORD record: ord-59174d073201402aaefbbf8df9f5083e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423036B2

Reaction notes

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