p-Toluenesulfonic acid monohydrate → 2-(2-Fluoro-5-nitrophenyl)-5-phenylbenzoxazole

HRID 722519Notes

Reaction equation

HRID 722519 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5](Br)=[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.[C:23]1(C)[CH:28]=[CH:27][C:26](S(O)(=O)=O)=[CH:25][CH:24]=1>>[N+:17]([C:15]1[CH:16]=[C:11]([C:10]2[O:21][C:2]3[CH:7]=[CH:6][C:5]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[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 21884381N-(2-hydroxy-5-bromophenyl)-2-fluoro-5-nitrobenzamide

Product 1

HCID 218843342-(2-Fluoro-5-nitrophenyl)-5-phenylbenzoxazole

Procedure

Prepared by the method of Example 15c), from N-(2-hydroxy-5-bromophenyl)-2-fluoro-5-nitrobenzamide (11.0 g, 0.03 mol) and p-toluenesulfonic acid monohydrate (11.88 g, 0.06 mol) the subtitle compound was obtained (6 g, 58%). 1H NMR (DMSO) δ 8.98(dd, 1H), 8.54(m, 1H), 8.19(d, 1H), 7.97(d, 1H), 7.81(m, 4H), 7.52(t, 2H), 7.42(d, 1H).

Sources & evidence

ORD record
ord-326d3265b42b4eb1917917ef2323126a
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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