Water → HCID 3089143, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=O)=[CH:17][CH:16]=1)([O-:14])=[O:13].O>COCCOCCOC>[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19]2[O:11][C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[N:1]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
2-Amino-4-nitrophenol (46.2 g, 0.3 mol) was dissolved in diglyme (1250 mL) and added to a 3-necked, 3-liter flask equipped with a condenser, a mechanical stirrer, and a hearer. 4-Nitrobenzoyl chloride (57 g, 0.3 mol) was dissolved in diglyme (250 mL) and added to the flask. The mixture was heated, with stirring, to 120° C. for 1 hour, whereupon polyphosphoric acid (90 g) was added. Heating was continued at 150° C. to 160° C. for an additional 1 hour. The reaction mixture was cooled to 110° C. to 120° C. and deionized water (500 mL) was added over a period of 15 to 30 minutes while the mixture was maintained at 100° C. The reaction mixture was cooled, and the precipitated product was filtered and washed with methanol (300 mL), then dried. The melting point was found to be 253° C. to 255° C. The overall yield was 95 percent with an assay of 100 percent by liquid chromatography.
Workup
- additionadded to a 3-necked, 3-liter flask
- customequipped with a condenser, a mechanical stirrer
- additionadded to the flask
- temperatureThe mixture was heated
- additionwas added
- temperatureHeating
- temperatureThe reaction mixture was cooled to 110° C. to 120° C.
- temperatureThe reaction mixture was cooled
- filtrationthe precipitated product was filtered
- washwashed with methanol (300 mL)
- customdried
- customto be 253° C. to 255° C
Sources & evidence
- ORD record
- ord-23dc5eb49a064112bc4c153933e57119
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05739344
Reaction notes
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