Acetic Anhydride → N-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]formamide
Reaction equation
[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:15]([O-])=[O:16].[Na+].C(OC(=O)C)(=O)C>C(O)=O>[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]=[O:16])=[CH:10][CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
(a-4) To a stirred solution of 15 parts of 4-[1-(1H-imidazol-1-yl)ethyl]-benzenamine and 2.7 parts of sodium formate in 60 parts of formic acid is added dropwise a solution of 9 parts of acetic acid anhydride in 24 parts of formic acid at 50° C. The reaction mixture was stirred for 1 hour at 100° C. and the solvent was evaporated. The residue was dissolved in a small amount of ice water and the solution was treated with ammonium hydroxide while cooling. The product was extracted twice with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized twice from tetrahydrofuran, yielding 13.8 parts (80%) of N-[4-[1-(1H-imidazol-1-yl)ethyl]phenyl]-formamide; mp. 129.4° C. (int. 115).
Workup
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in a small amount of ice water
- additionthe solution was treated with ammonium hydroxide
- temperaturewhile cooling
- extractionThe product was extracted twice with dichloromethane
- customThe combined extracts were dried
- filtrationfiltered
- customevaporated
- customThe residue was crystallized twice from tetrahydrofuran
Sources & evidence
- ORD record
- ord-7376947100e44175beb11a11710ceb16
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859684
Reaction notes
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