Acetic Anhydride → HCID 57552284, compound
Reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:8]=2[C:9]#[N:10])=[CH:4][C:3]=1[CH3:18].[C:19]([O-:22])(=O)[CH3:20].[K+].C(OC(=O)C)(=O)C.[N:31](OCCC(C)C)=O>C1(C)C=CC=CC=1>[C:19]([N:1]1[C:2]2[C:3](=[CH:4][C:5]([O:6][C:7]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:8]=3[C:9]#[N:10])=[CH:16][CH:17]=2)[CH:18]=[N:31]1)(=[O:22])[CH3:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 2 L flask, 2-(4-amino-3-methylphenoxy)-5-fluorobenzonitrile (277.1 ml, 221.7 mmol) was taken up in toluene (0.8 M) and treated with potassium acetate (26.11 g, 266.0 mmol) at ambient temperature. The reaction mixture was cooled to 0° C. and acetic anhydride (63.91 mL, 676.1 mmol) was added over 2 minutes. The ice bath was removed, the flask was fitted with a reflux condenser and the reaction was heated to 40° C. Isoamyl nitrite (59.29 mL, 443.3 mmol) was added dropwise. The reaction was heated to reflux for 15 hours, cooled to ambient temperature, and concentrated. The resulting solids were suspended in 2 L water, stirred vigorously for 15 minutes, filtered, and washed with water (1 L). The resulting solid (75 g, still wet) was used directly in the next step.
Workup
- customThe ice bath was removed
- customthe flask was fitted with a reflux condenser
- temperaturethe reaction was heated to 40° C
- temperatureThe reaction was heated
- temperatureto reflux for 15 hours
- temperaturecooled to ambient temperature
- concentrationconcentrated
- filtrationfiltered
- washwashed with water (1 L)
Sources & evidence
- ORD record
- ord-607f5503fb6b4b889cfac41d3cc4a22a
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202899B2
Reaction notes
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