Methanesulfenyl chloride, trifluoro- → HCID 20378259, compound

HRID 2051942Notes

Reaction equation

HRID 2051942 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[F:32][C:33]([F:37])([F:36])[S:34]Cl.C(=O)(O)[O-].[Na+]>C1COCC1.CCOCC.CCCCCC.O>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:12]=[C:11]1[S:34][C:33]([F:37])([F:36])[F:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 67900Methanesulfenyl chloride, trifluoro-HCID 516892Sodium BicarbonateHCID 20349435HCID 20349435, compoundHCID 178418339Butyllithium

Product 1

HCID 20378259HCID 20378259, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

In glassware dried with a heat gun and under nitrogen, to a mixture of 1.7 g (5 mmole) of 1-benzyloxymethyl-4,5-diphenylimidazole in 25 ml THF and 25 ml ether at -78° was added dropwise a solution of 3.75 ml of 1.6 M n-butyl lithium solution in hexane in 25 ml ether. The reaction mixture was stirred at -78° ca. 15 minutes then 0.8 g (6 mmole) of trifluoromethanesulfenyl chloride (TOXIC) was added as a gas. The mixture was stirred at -78° for 2 hours, then RT overnight. The mixture was added to 200 ml water and neutralized with sodium bicarbonate. The mixture was extracted with ether and the ether extracts were dried and concentrated. The residue was chromatographed on 200 g SilicAR CC-7, eluting with toluene to give, after recrystallization from hexane, 0.5 g (23%) of product, mp 97°-8°.

Workup

  1. stirringThe mixture was stirred at -78° for 2 hours
  2. customRT overnight
  3. extractionThe mixture was extracted with ether
  4. dry with materialthe ether extracts were dried
  5. concentrationconcentrated
  6. customThe residue was chromatographed on 200 g SilicAR CC-7
  7. washeluting with toluene
  8. customto give
  9. customafter recrystallization from hexane, 0.5 g (23%) of product, mp 97°-8°

Sources & evidence

ORD record
ord-fd9ba5becae2416f99d05a3545a0097e
Source dataset
uspto-grants-1980_01
Patent number
US04182769

Reaction notes

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