Methyl formate → Formamide, N-((5H-dibenzo(a,d)cyclohepten-5-yl)methyl)-
Reaction equation
[NH2:1][CH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.[CH3:18][O:19]C=O>>[CH:18]([NH:1][CH2:2][CH:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[CH:6]=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)=[O:19]Participants
Conditions
- Temperature
- 110 °C
Procedure
5-Aminomethyl-5H-dibenzo[a,d]cycloheptene (4.82 g., 0.0218 mole) and methylformate, 200 ml. are heated to 110° C. for 161/2 hours in an autoclave. The yellow solution is evaporated to dryness on a film evaporator under reduced pressure. The residue is dissolved in benzene, the solution extracted with dilute hydrochloric acid, then with water and dried over anhydrous sodium sulfate. The benzene is evaporated and the residue dried to constant weight in a film evaporator under reduced pressure. The yellow solid residue weighs 5.49 g. and melts at 115°-117.5° C. to a cloudy melt, clearing at 119° C. Recrystallization from mixtures of benzene and hexane, followed by recrystallization from mixtures of ethanol and water gives a product melting at 120.3°-121° C. (clears 121.8° C.).
Workup
- customThe yellow solution is evaporated to dryness on a film evaporator under reduced pressure
- dissolutionThe residue is dissolved in benzene
- extractionthe solution extracted with dilute hydrochloric acid
- dry with materialwith water and dried over anhydrous sodium sulfate
- customThe benzene is evaporated
- customthe residue dried to constant weight in a film evaporator under reduced pressure
- customclearing at 119° C
- customRecrystallization from mixtures of benzene and hexane
- customfollowed by recrystallization from mixtures of ethanol and water
Sources & evidence
- ORD record
- ord-2d19c565c66b452e9c6bff4bb020ef6f
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03992445
Reaction notes
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