Methanol → 1-Methyl-3-methylthiomethyl-7-trifluoromethyl-4-quinolone

HRID 325624Notes

Reaction equation

HRID 325624 reaction equation
Cl.Cl[CH2:3][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:10][CH:11]=2)[N:6]([CH3:19])[CH:5]=1.[CH3:20][S-:21].[Na+].CO>O>[CH3:19][N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([C:15]([F:18])([F:17])[F:16])[CH:8]=2)[C:13](=[O:14])[C:4]([CH2:3][S:21][CH3:20])=[CH:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4378561Sodium methanethiolateHCID 136693393-Chloromethyl-1-methyl-7-trifluoromethyl-4-quinolone hydrochloride

Product 1

HCID 128078421-Methyl-3-methylthiomethyl-7-trifluoromethyl-4-quinolone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chloromethyl-1-methyl-7-trifluoromethyl-4-quinolone hydrochloride (4.7 g.) was added to a stirred solution of sodium methanethiolate in methanol (16 ml. containing 0.039 mole NaSMe) at 0° during 5 minutes. The resulting mixture was allowed to warm to room temperature then poured into water (100 ml.). The resulting precipitate was collected, dried and crystallised from dichloromethane:petroleum ether (b.p. 60°-80°) to give the novel 1-methyl-3-methylthiomethyl-7-trifluoromethyl-4-quinolone, m.p. 182°-184°.

Workup

  1. customThe resulting precipitate was collected
  2. customdried
  3. customcrystallised from dichloromethane

Sources & evidence

ORD record
ord-4371689401014d3c8f4353e37471daae
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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