Nitric Acid → 2-Chlorobenzoxazole

HRID 1580681Notes

Reaction equation

HRID 1580681 reaction equation
[N+](C1C=CC(N)=CC=1)([O-])=O.[Cl:11][C:12]1[O:13][C:14]2[CH:20]=[C:19]([N+]([O-])=O)[CH:18]=[CH:17][C:15]=2[N:16]=1.[N+]([O-])(O)=O>O1CCOCC1.S(=O)(=O)(O)O>[Cl:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 74754-NitroanilineHCID 10750488HCID 10750488, compound

Product 1

HCID 119862-ChlorobenzoxazoleYield 44.4%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 83 g of p-nitroaniline in 400 ml of dioxane is added at room temperature, with stirring, to 126 g of 2-chloro-6-nitrobenzoxazole obtained from 43.3 g of 2-chlorobenzoxazole with fuming nitric acid (d. 1.52) in sulphuric acid. The solution is heated to 40°C and stirred at this temperature for a further 19 hours. The solution is diluted with 200 ml of water; it is then cooled and the precipitate separated. The suction-filter residue is dried and dissolved in 500 ml of dimethylformamide. This solution is purified, and diluted with 200 ml of ethanol. The precipitating 6-nitro-2-(4'-nitroanilino)-benzoxazole has the melting point 305° to 310°C.

Sources & evidence

ORD record
ord-380b4752eee744cf8cf664b35c4a7dc6
Source dataset
uspto-grants-1976_01
Patent number
US03933841

Reaction notes

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