Hydrochloric Acid → HCID 86644106, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14](N)=[CH:15][CH:16]=3)[O:11][C:10]([CH3:20])([CH3:19])[CH:9]=2)=[CH:4][CH:3]=1.[ClH:21].N([O-])=O.[Na+].[S:26](=[O:28])=[O:27]>C(#N)C.O.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:26]([Cl:21])(=[O:28])=[O:27])=[CH:15][CH:16]=3)[O:11][C:10]([CH3:20])([CH3:19])[CH:9]=2)=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 5 °C
Procedure
To a solution of the compound obtained in (5) described above (1.5 g) in acetonitrile (30 mL) was added acetic acid (2.62 mL) and then thereto was added hydrochloric acid (2.62 mL) over a period of 2 minutes at room temperature. To the mixture was added an aqueous solution of sodium nitrite (4.24 g) in water (1.62 mL) over a period of one minute, and the mixture was stirred at 5° C. for 20 minutes. The reaction vessel was pressurized with sulfur dioxide gas for 35 minutes (the inner temperature was below 10° C.). Then an aqueous solution (1.62 mL) of cupric chloride(II) (754 mg) was added to the reaction solution, and the mixture was stirred at room temperature for one hour. Water (30 mL) was added to the reaction solution, and the mixture was extracted with dichloromethane (30 mL×3). The combined organic layer was washed successively with water and brine, dried over sodium sulfate and concentrated in vacuo to give the titled compound (2 g) as a crude product, which was used in the next step without further purification.
Workup
- customwas below 10° C.
- stirringthe mixture was stirred at room temperature for one hour
- extractionthe mixture was extracted with dichloromethane (30 mL×3)
- washThe combined organic layer was washed successively with water and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-418943947ac3487ca62d8f244a36d0d6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410166B2
Reaction notes
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