Sodium methanethiolate → HCID 86747006, compound

HRID 1588803Notes

Reaction equation

HRID 1588803 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4](Cl)[C:3]=1[N:13]1[C:17]([S:18]([CH:21]([F:23])[F:22])(=[O:20])=[O:19])=[C:16]([Cl:24])[N:15]=[C:14]1[Br:25].[CH3:26][S-:27].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[C:3]([N:13]2[C:17]([S:18]([CH:21]([F:23])[F:22])(=[O:20])=[O:19])=[C:16]([Cl:24])[N:15]=[C:14]2[Br:25])=[C:4]([S:27][CH3:26])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86747007HCID 86747007, compound

Product 1

HCID 86747006HCID 86747006, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 500 mg (0.984 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-bromo-4-chlorodifluoromethylsulfonyl-imidazole in 2 ml of tetrahydrofuran was added a solution of 69 mg (0.984 mmole) of sodium methanethiolate in 0.3 ml of water. The resulting mixture was stirred at RT for 14 hours, after which it was partitioned between water and diethyl ether. The organic layer was separated, dried over anhydrous sodium sulfate and stripped of solvent. The residue was purified by preparative TLC using 20% ethyl acetate in hexane to give 180 mg (35% yield) of the product, mp 116° C.

Workup

  1. customafter which it was partitioned between water and diethyl ether
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-8a38652fbd284b43bd7bb710e60a587e
Source dataset
uspto-grants-1993_06
Patent number
US05223525

Reaction notes

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