Sodium hydride → HCID 54152133, compound

HRID 864549Notes

Reaction equation

HRID 864549 reaction equation
[CH2:1]([O:3][C:4]([NH:6][N:7]=[C:8]([C:16]1[CH:21]=[CH:20][C:19]([O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:5])[CH3:2].[H-].[Na+].[H][H].Cl[C:35]([N:38]([S:46]N(C(Cl)(C)C)CCC(OCC)=O)[CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])([CH3:37])[CH3:36]>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]([S:46][N:38]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:35]([CH3:36])[CH3:37])[N:7]=[C:8]([C:16]1[CH:21]=[CH:20][C:19]([O:22][S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 53769132HCID 53769132, compoundHCID 131719603HCID 131719603, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54152133HCID 54152133, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-4'-trifiuoromethyls ulfonyloxybenzophenone-N-ethoxycarbonylhydrazone (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'-trifluoromethylsulfonyloxybenzo- phenone-N-ethoxycarbonyl-N-{N'-(2-ethoxycarbonylethyl)-N'-isopropylaminosulfenyl }-hydrazone (compound 28).

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-2d8e961ffa9a4924888e0ffd728ce116
Source dataset
uspto-grants-1996_10
Patent number
US05563174

Reaction notes

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