P-Toluenesulfonylhydrazide → N'-(dihydro-2H-pyran-4(3H)-ylidene)-4-methylbenzenesulfonohydrazide

HRID 331140Notes

Reaction equation

HRID 331140 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][NH2:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[O:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][N:12]=[C:16]2[CH2:17][CH2:18][O:13][CH2:14][CH2:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 15303P-ToluenesulfonylhydrazideHCID 121599Tetrahydro-4H-pyran-4-one

Product 1

HCID 68380128N'-(dihydro-2H-pyran-4(3H)-ylidene)-4-methylbenzenesulfonohydrazideYield 40.2%

Procedure

A solution of 4-methylbenzenesulfonohydrazide (819 mg, 4.4 mmol) and dihydro-2H-pyran-4(3H)-one (487 μl, 5.28 mmol) was stirred in a Dean-Stark apparatus at 120° C. for 24 hours. The reaction mixture was cooled and evaporated at reduced pressure. The residue was purified by chromatography using a gradient of dichloromethane/ethyl acetate=100:0 to 80:20 as the eluent to give the 4-methyl-N′-(2H-pyran-4(3H,5H,6H)-ylidene)benzenesulfonohydrazide (475 mg, 40% yield) as an off white solid. MS (ISP): m/z=269.3 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated at reduced pressure
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-fe0641c0e2414a21a8007f9a32cbab72
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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