Trimellitic anhydride → 2-[2-Methoxy-5-[5-(2-benzothiopheneyl)benzoxazol-2-yl]phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

HRID 722626Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[S:20][C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[CH:23]=4)=[CH:15][C:13]=3[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:28]1[C:33]([C:34]([OH:36])=[O:35])=[CH:32][C:31]2[C:37]([O:39][C:40](=O)[C:30]=2[CH:29]=1)=[O:38]>>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]4[S:20][C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[CH:23]=4)=[CH:15][C:13]=3[N:14]=2)=[CH:3][C:2]=1[N:1]1[C:37](=[O:38])[C:31]2[C:30](=[CH:29][CH:28]=[C:33]([C:34]([OH:36])=[O:35])[CH:32]=2)[C:40]1=[O:39]

Participants

Reactant 2

HCID 11089Trimellitic anhydride

HCID 218845732-(3-Amino-4-methoxyphenyl)-5-(2-benzothiophenyl)benzoxazole

Product 1

HCID 218845022-[2-Methoxy-5-[5-(2-benzothiopheneyl)benzoxazol-2-yl]phenyl]-1,3-dioxo-2,3-dihydro-1h-isoindole-5-carboxylic acid

Procedure

Prepared by the method of Example 15f), from 2-(3-amino-4-methoxyphenyl-5-(2-benzothiophenyl)benzoxazole (120 mg, 0.32 mmol) and 1,2,4-benzenetricarboxylic anhydride (62 mg, 0.32 mmol) the title compound was obtained. (41 mg, 23%). 1H NMR (DMSO) δ 13.82(s, 1H), 8.46(dd, 1H), 8.38(d, 1H), 8.35(m, 2H), 8.18(d, 1H), 8.13(d, 1H), 8.00(d, 1H), 7.96(s, 1H), 7.85(m, 3H), 7.50(d, 1H), 7.40(m, 2H), 3.90(s, 3H). MS 547.2 m/z (M+H)+.

Sources & evidence

ORD record: ord-41a73653c82f4d19a3166f50fc594547
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

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