Phosphorus oxychloride → HCID 57457877, compound
Reaction equation
P(Cl)(Cl)(Cl)=O.ClC1[N+]([O-])=NC([O:14][C:15]2[C:20]([CH:21]=[CH2:22])=[C:19](C)[CH:18]=[C:17](C)[C:16]=2C)=CC=1.[Cl:26][C:27]1N=[N+]([O-])C(OC2C(C=C)=C(C)C=C(C)C=2C)=[CH:31][CH:32]=1>>[Cl:26][CH2:27][CH2:32][CH2:31][CH:22]1[CH2:21][C:20]2[C:19]1=[CH:18][CH:17]=[CH:16][C:15]=2[OH:14]Participants
Procedure
0.02 mL (0.22 mmol) of phosphorus oxychloride was added to 27.6 mg (0.0949 mmol) of a mixture of 6-chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine 1-oxide and 3-chloro-6-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine 1-oxide obtained in (6), and the resulting mixture was stirred at room temperature for 2 hours. To the mixture was added 0.4 mL of chloroform, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated, 0.2 mL (2.2 mmol) of phosphorus oxychloride was added to the residue and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated, the residue was purified by preparative thin-layer chromatography (available from MERCK CO., 1.05744, 1 plate was used, developed by hexane:ethyl acetate=5:1) to obtain 5.0 mg (0.016 mmol, Yield: 17%) of 4,6-dichloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine.
Sources & evidence
- ORD record
- ord-395ab50371a34505a3caf402360a427a
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608563B2
Reaction notes
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