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

HRID 2291012Notes

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.Cl.C(=O)([O-])[O-].[Na+].[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

Then, 4.32 g (0.01 mol) of 2,4,5-tris(4-nitrophenyl)oxazole was mixed with 200 ml of N,N-dimethylformamide and 8 g of an iron powder (reduced iron available from Wako Pure Chemical Industries, Ltd.). To the resulting mixture, 4 ml of concentrated hydrochloric acid and 12 ml of water were added, and the mixture was heated to 100° C. while stirring well. After reacting for 1 hour, the reacting solution was neutralized to pH: 8 with a saturated aqueous solution of sodium carbonate, and while maintained at 100° C., it was filtered in a heated state. The filtrate was poured into 1 l of iced water. The white precipitate formed of 2,4,5-tris(4-aminophenyl)oxazole was filtered off and dried. Yield: 3.27 g (96%).

Workup

temperaturewhile maintained at 100° C.
filtrationit was filtered in a heated state
additionThe filtrate was poured into 1 l of iced water

Sources & evidence

ORD record: ord-2032d3b4acb44142b85a50e617b0c98f
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04619881

Reaction notes

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