Thionyl Chloride → HCID 70221442, compound

HRID 581996Notes

Reaction equation

HRID 581996 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:15]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)O)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2>C(Cl)Cl>[Cl:5][C:6]1[C:15]([CH:16]([Cl:3])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 70218487HCID 70218487, compound

Product 1

HCID 70221442HCID 70221442, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (8 ml) was added dropwise to a solution of intermediate 5 (8 g) in CH2Cl2 (400 ml) at 0° C. and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was partitioned between CH2Cl2 and water which was alkalized with a saturated K2CO3 solution. The separated organic layer was dried over MgSO4, filtered and the filtrate evaporated, yielding 8.4 g (100%) (±)-5-chloro-6-[chloro[3-(trifluoromethyl) phenyl]methyl]quinoline (intermediate 6).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between CH2Cl2 and water which
  3. dry with materialThe separated organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-ee09b4573cb3422485cbfa722aa50243
Source dataset
uspto-grants-1999_07
Patent number
US05922734

Reaction notes

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