Phenol → HCID 20264370, compound

HRID 463605Notes

Reaction equation

[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[C:9](F)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])=[O:3].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[C:9]([O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])=[O:3]

Participants

Reactant 3

HCID 996Phenol

HCID 11430Potassium Carbonate

HCID 16641156N-(5-Fluoro-2-nitrophenyl)acetamide

Product 1

HCID 20264370HCID 20264370, compound

Procedure

Following the procedure of Example 4, N-methylcarbonyl 2-nitro-5-fluoroaniline (1.0 g, 5.1 mmol), phenol (0.47 g, 5.1 mmol) and potassium carbonate (1.4 g, 10.2 mmol) are reacted together to give N-methylcarbonyl 2-nitro-5-phenoxyaniline, 1.2 g of which is then reacted with 20% hydrochloric acid (50 ml) to give 2-nitro-5-phenoxyaniline. The 2-nitro-5-phenoxyaniline (0.9 g, 3.9 mmol) is reacted with potassium hydroxide (0.2 g, 3.9 mmol) and sodium hypochlorite (11 ml of 5.2% solution, 0.6 g, 7.8 mmol) to yield 5-phenoxybenzo-2,1,3-oxadiazole N-oxide, m.p. 76°-77°.

Workup

customare reacted together

Sources & evidence

ORD record: ord-d63651e7578a417885cd693d99559072
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04544400

Reaction notes

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