Sodium hydride → HCID 131719604, compound

HRID 864550Notes

Reaction equation

HRID 864550 reaction equation
[C:1]([NH:4][N:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[H-].[Na+].[H][H].Cl[C:33]([N:36]([S:44]N(C(Cl)(C)C)CCC(OCC)=O)[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])([CH3:35])[CH3:34]>O1CCCC1>[C:1]([N:4]([S:44][N:36]([CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:33]([CH3:34])[CH3:35])[N:5]=[C:6]([C:14]1[CH:19]=[CH:18][C:17]([O:20][S:21]([C:24]([F:25])([F:27])[F:26])(=[O:23])=[O:22])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 54408928HCID 54408928, compoundHCID 131719603HCID 131719603, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131719604HCID 131719604, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-4'-trifluoromethylsulfonyloxybenzophenone-N-acetylhydrazone (0.5 g) in tetrahydrofuran (6 ml) was stirred at room temperature under a nitrogen atmosphere, during which an oily mixture (50 mg) of sodium hydride containing 60% (w/w) sodium hydride was added to the solution at a time. After stirring at room temperature for 15 minutes and finding no evolution of hydrogen gas, the mixture was cooled to -78° C., and chloro-{N-(2-ethoxycarbonylethyl)-N-isopropylamino}sulfide (0.3 g) was added dropwise over 3 minutes. The reaction mixture was warmed to room temperature over 4 hours, and then poured into ice-water. Further, a saturated saline solution was added thereto. The aqueous layer was extracted with ethyl acetate, and the extract was combined with the organic layer. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 0.2 g of 4-chloro-4'-trifluoromethylsulfonyloxybenzophenone -N-ac etyl -N- {N '-(2-ethoxycarbonylethyl)-N'-isopropylaminosulfenyl}hydrazone (compound 24).

Workup

  1. additionwas added to the solution at a time
  2. temperaturethe mixture was cooled to -78° C.
  3. temperatureThe reaction mixture was warmed to room temperature over 4 hours
  4. additionFurther, a saturated saline solution was added
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45ce8612137c48b49da82d6639c14eb3
Source dataset
uspto-grants-1996_10
Patent number
US05563174

Reaction notes

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