Thionyl Chloride → HCID 19592939, compound

HRID 613519Notes

Reaction equation

HRID 613519 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:7]=1[C:8]([NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][C:17]([CH:21]=[CH2:22])=[C:16]2[CH2:23]O)=[O:9].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:3][CH2:23][C:16]1[C:15]2[C:20](=[C:11]([NH:10][C:8](=[O:9])[C:7]3[C:6]([Cl:5])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:29])[CH:12]=[CH:13][CH:14]=2)[N:19]=[CH:18][C:17]=1[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 19592996HCID 19592996, compound

Product 1

HCID 19592939HCID 19592939, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N,N-dimethylformamide (1 ml) was added thionyl chloride (73.2 mg), and the mixture was stirred for 15 minutes at ambient temperature. To the mixture was added 8-(2,6-dichlorobenzoylamino)-4-hydroxymethyl-3-vinylquinoline (176.7 mg), and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added saturated sodium bicarbonate solution (10 ml) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature. The resulting precipitate was collected by filtration and washed with water to give 4-chloromethyl-8-(2,6-dichlorobenzoylamino)-3-vinylquinoline (182.8 mg).

Workup

  1. stirringthe mixture was stirred for 30 minutes at ambient temperature
  2. temperaturecooling
  3. stirringthe mixture was stirred for 15 minutes at the same temperature
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-65dbf75d6b6d4014a4c24d4d9d368ce4
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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