Trimellitic anhydride → HCID 58743025, compound

HRID 722657Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]5[O:27][CH2:28][O:29][C:23]=5[CH:22]=4)=[CH:17][C:15]=3[N:16]=2)[C:5]([NH:8][CH2:9][CH2:10][CH3:11])=[CH:6][CH:7]=1.[CH:30]1[C:35]([C:36]([OH:38])=[O:37])=[CH:34][C:33]2[C:39]([O:41][C:42](=O)[C:32]=2[CH:31]=1)=[O:40]>>[CH2:9]([NH:8][C:5]1[C:4]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]5[O:27][CH2:28][O:29][C:23]=5[CH:22]=4)=[CH:17][C:15]=3[N:16]=2)=[CH:3][C:2]([N:1]2[C:39](=[O:40])[C:33]3[C:32](=[CH:31][CH:30]=[C:35]([C:36]([OH:38])=[O:37])[CH:34]=3)[C:42]2=[O:41])=[CH:7][CH:6]=1)[CH2:10][CH3:11]

Participants

Reactant 2

HCID 11089Trimellitic anhydride

HCID 69585074HCID 69585074, compound

Product 1

HCID 58743025HCID 58743025, compound

Procedure

Prepared by the method of Example 15f), from 2-(3-amino-6-propylaminophenyl)-5-(3,4-methylenedioxyphenyl)benzoxazole (157 mg, 0.40 mmol) and 1,2,4-benzenetricarboxylic anhydride (76 mg, 0.40 mmol) the title compound was obtained (82 mg, 36%). 1H NMR (DMSO) δ 13.78(s, 1H), 8.49(t, 1H), 8.42(dd, 1H), 8.30(s, 1H), 8.12(d, 1H), 8.07(d, 1H), 8.00(d, 1H), 7.78(d, 1H), 7.64(dd, 1H), 7.47(dd, 1H), 7.35(d, 1H), 7.24(dd, 1H), 7.04(d, 1H), 7.01(d, 1H), 6.08(s, 2H), 3.35(m, 2H), 1.76(m, 2H), 1.07(t, 3H). MS 562.2 m/z (M+H)+.

Sources & evidence

ORD record: ord-b409049ceb8e4bf5ae91bf9bd0b62bd8
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138425B2

Reaction notes

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