Hydrochloric Acid → HCID 86644106, compound

HRID 2380909Notes

Reaction equation

HRID 2380909 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]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 23668193Sodium NitriteHCID 59443017HCID 59443017, compound

Product 1

HCID 86644106HCID 86644106, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

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

  1. customwas below 10° C.
  2. stirringthe mixture was stirred at room temperature for one hour
  3. extractionthe mixture was extracted with dichloromethane (30 mL×3)
  4. washThe combined organic layer was washed successively with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-715a507e21a64fd197755c162294c0ed
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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