Pyridine → HCID 54560567, compound
Reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.ClCl.[Cl:9][CH2:10][C:11](=[O:16])CC(Cl)=O.[C:17]1([S:23]C(O)C)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl.O>[Cl:9][CH2:10][C:11](=[O:16])[CH2:3][C:4]([O:6][CH2:2][CH2:1][S:23][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:5]Participants
Procedure
In 100 ml of methylene chloride was dissolved 35.4 g (0.421 mole) of diketene. The solution was cooled to -30° to -35° C. and 29.5 g (0.415 mole) of chlorine was bubbled into the solution for about an hour to prepare 4-chloroacetoacetyl chloride. The solution was cooled to 40° C. or below and a solution of 50 g (0.324 mole) of phenylthioethanol and 25.6 g (0.324 mole) of pyridine in 52 ml of methylene chloride was added dropwise to the solution at -20° C. or below over a period of about an hour. After completion of addition, the reaction was allowed to proceed at -5° C. for about an hour. To the reaction mixture were added 400 ml of methylene chloride and 700 ml of water to extract the reaction product. The aqueous layer was further extracted with 200 ml of methylene chloride. The organic layers were combined, washed with water and concentrated to dryness under reduced pressure to give 88.5 g of phenylthioethyl 4-chloroacetoacetate as an oil.
Workup
- temperatureThe solution was cooled to -30° to -35° C.
- temperatureThe solution was cooled to 40° C. or below
- additionAfter completion of addition
- waitto proceed at -5° C. for about an hour
- extractionto extract the reaction product
- extractionThe aqueous layer was further extracted with 200 ml of methylene chloride
- washwashed with water
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-0bb5cd4f7f3948acb40a1658db250ae0
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04695639
Reaction notes
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