Thionyl Chloride → Ethyl 4-(3-chlorophenyl)-6-[chloro(4-phenyl-2-thiazolyl)methyl]-1,2-dihydro-2-oxo-3-quinolinecarboxylate

HRID 1830808Notes

Reaction equation

HRID 1830808 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22](O)[C:23]4[S:24][CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:27]=4)[CH:20]=3)[NH:15][C:14](=[O:35])[C:13]=2[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:9]=[CH:10][CH:11]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22]([Cl:3])[C:23]4[S:24][CH:25]=[C:26]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:27]=4)[CH:20]=3)[NH:15][C:14](=[O:35])[C:13]=2[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22048469Ethyl 4-(3-chlorophenyl)-1,2-dihydro-6-[hydroxy(4-phenyl-2-thiazolyl)methyl]-2-oxo-3-quinolinecarboxylate

Product 1

HCID 22048490Ethyl 4-(3-chlorophenyl)-6-[chloro(4-phenyl-2-thiazolyl)methyl]-1,2-dihydro-2-oxo-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (30 ml) was added dropwise to a mixture of intermediate (19) (0.0245 mol) in DCM (150 ml), previously cooled on an ice bath. The mixture was stirred at a low temperature for 1 hour and at room temperature overnight. The solvent was evaporated till dryness. The product was used without further purification, yielding (quant.) of ethyl 4-(3-chlorophenyl)-6-[chloro(4-phenyl-2-thiazolyl)methyl]-1,2-dihydro-2-oxo-3-quinolinecarboxylate (intermediate 20).

Workup

  1. temperaturepreviously cooled on an ice bath
  2. customThe solvent was evaporated till dryness
  3. customThe product was used without further purification

Sources & evidence

ORD record
ord-94fa4a152fa74fb790ae8939a000929a
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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