Sulfuric Acid → 2,4,5-Tris(4-aminophenyl)oxazole

HRID 64992Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-])=O.CN(C)C=O.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][C:12]([C:24]3[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=3)=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=3)[N:14]=2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

13 g (0.03 mol) of the 2,4,5-tris(4'-nitrophenyl)oxazole was mixed with 500 ml of N,N-dimethylformamide and 26 g of iron powder. The mixture thus obtained was admixed with 10 ml of concentrated sulfuric acid and 30 ml of water, and then heated to a temperature of 100° C. with stirring. After 1 hour passed, the mixture was neutralized with a saturated aqueous solution of sodium bicarbonate with the reaction temperature kept at a temperature of 100° C. The pH of the solution after the reaction was adjusted to 8. The reaction solution was hot-filtered, and the filtrate was then poured into 3 l of ice water to produce a light yellow precipitate of 2,4,5-tris(4'-aminophenyl)oxazole which was then filtered off and dried to obtain 4.47 g of the product (yield: 97%).

Workup

customThe mixture thus obtained
customkept at a temperature of 100° C
filtrationThe reaction solution was hot-filtered
additionthe filtrate was then poured into 3 l of ice water

Sources & evidence

ORD record: ord-ed5e16e0692f418aa3122b2b9aaa6ff9
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04612271

Reaction notes

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