2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 2-(4-(trifluoromethyl)phenyl)oxazole-4-carboxylate

HRID 891056Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][CH:12]([C:14]([O:16][CH3:17])=[O:15])[N:13]=2)=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:13]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate (1.33 g, 4.87 mmol) was stirred in toluene (60 ml) at 55° C. until all of the starting material was dissolved. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (5.53 g, 24.365 mmol) was then added in portions, and the resulting solution was stirred at 75° C. for 36 hours. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography, to provide methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxylate, a compound of formula (15). D. Preparation of a Compound of Formula (16)

Workup

dissolutionwas dissolved
customThe solvent was evaporated under reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-6318067dfd82486aa164581de115104d
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001909B2

Reaction notes

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