Carbon Tetrachloride → HCID 178516749, compound
Reaction equation
[C:1]([O:13]C)(=O)[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.O.[NH2:40][NH2:41]>C1COCC1.O>[C:6]1([C:4]2[NH:3][CH2:2][C:1](=[O:13])[NH:41][N:40]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
7
Conditions
- Temperature
- 50 °C
Procedure
To 5.8 g. of methyl hippurate dissolved in 35 ml THF was added 3.9 g. of triphenylphosphine and 10.0 g. of carbon tetrachloride in 15 ml THF. The mixture was heated to about 50° C. for 6 hours and 3.0 g. of hydrazine hydrate was added. The mixture was refluxed for about 18 hours, cooled and poured into water. The solution was extracted with ethyl acetate, and the organic phase was then extracted with 1 N HCl. The acidic extract was neutralized with 6 N sodium hydroxide and the product was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid was recrystallized from methanol to yield about 0.200 g. of solid. Yield 4%. M.P.=212°-216° C.
Workup
- additionwas added 3.9 g
- temperatureThe mixture was refluxed for about 18 hours
- temperaturecooled
- extractionThe solution was extracted with ethyl acetate
- extractionthe organic phase was then extracted with 1 N HCl
- extractionThe acidic extract
- extractionthe product was extracted with ethyl acetate
- dry with materialThe organic phase was dried over anhydrous magnesium sulfate
- concentrationconcentrated under vacuum
- customThe solid was recrystallized from methanol
- customto yield about 0.200 g
Sources & evidence
- ORD record
- ord-c044782e74f04c02a92de12e53bcc028
- Source dataset
- uspto-grants-1982_12
- Patent number
- US04362550
Reaction notes
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