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

HRID 64993Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S: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[S: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

15 g (0.034 mol) of the thus obtained 2,4,5-tris(4'-nitrophenyl)thiazole was mixed with 500 ml of N,N-dimethylformamide and 20 g of iron powder. The mixture was admixed with 10 ml of concentrated sulfuric acid and 30 ml of water. The admixture was heated to a temperature of 100° C. with thorough stirring. After 1 hour passed, the solution was neutralized with a saturated aqueous solution of sodium hydrogencarbonate with the reaction temperature kept at 100° C. to adjust the pH value thereof to 8. The reaction solution was then hot-filtered. The filtrate was poured into 3 l of ice water to produce a light yellow precipitate of 2,4,5-tris(4'-aminophenyl)thiazole which was then filtered off and dried to obtain 11.3 g (yield: 94%) of the product.

Workup

customkept at 100° C.
filtrationThe reaction solution was then hot-filtered
additionThe filtrate was poured into 3 l of ice water

Sources & evidence

ORD record: ord-5b1baca8eea241458711d6cdbea52488
Source dataset: uspto-grants-1986_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04612271

Reaction notes

Loading…