p-Toluenesulfonic acid monohydrate → 2-(3-Nitro-6-fluorophenyl)-5-fluorobenzoxazole

HRID 722588Notes

Reaction equation

HRID 722588 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:21])[C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[F:20].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[N+:17]([C:15]1[CH:16]=[C:11]([C:10]2[O:21][C:2]3[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=3[N:9]=2)[C:12]([F:20])=[CH:13][CH:14]=1)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21884478N-(2-Hydroxy-5-fluorophenyl)-2-fluoro-5-nitrobenzamide

Product 1

HCID 218843392-(3-Nitro-6-fluorophenyl)-5-fluorobenzoxazole

Procedure

Prepared by the method of Example 15b), from N-(2-hydroxy-5-fluorophenyl)-2-fluoro-5-nitrobenzamide (676 mg, 2.3 mmol) and p-toluenesulfonic acid monohydrate (961 g, 5.1 mmol) the subtitle compound was obtained (318 mg, 50%). 1H NMR (DMSO) δ 8.94(m, 1H), 8.54(m, 1H), 7.95(m, 1H), 7.81(m, 2H), 7.41(m, 1H).

Sources & evidence

ORD record
ord-89f4689cd2754a0db483bb81c2967789
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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