4-Toluenesulfonyl chloride → HCID 54438328, compound

HRID 1729098Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][N:8]=1)=[O:6].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C1COCC1>[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])[N:8]=1)=[O:6]

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of sodium hydride (4.6 g, 150 mmol, 80% in paraffin oil) indry THF (100 mL), a solution of 3-indazolecarboxylic acid methyl ester [(J.Am. Chem. soc, 74, 2009 (1952)] (22.0 g, 125 mmol) in dry THF (100 mL) was added dropwise with stirring while the inner temperature was maintained under 30° C. The reaction mixture was stirred for 30 minutes and then a solution of p-toluenesulphonyl chloride (28.0 g, 150 mmol) in dry THE (100 mL) was added dropwise to the stirring reactant. After 4 hours, the solvent was evaporated in vacuo and the residue partitioned between water and CH2Cl2. The organic phase was separated, dried over Na2SO4 and the solvent evaporated to leave a solid which was recrystallized from ethyl acetate (31.0 g, 75%), m.p. 163°-165° C.

Workup

stirringThe reaction mixture was stirred for 30 minutes
additionwas added dropwise to the stirring reactant
customthe solvent was evaporated in vacuo
customthe residue partitioned between water and CH2Cl2
customThe organic phase was separated
dry with materialdried over Na2SO4
customthe solvent evaporated
customto leave a solid which
customwas recrystallized from ethyl acetate (31.0 g, 75%), m.p. 163°-165° C.

Sources & evidence

ORD record: ord-e86650e12c334691bdfc9849e85976cb
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05331006

Reaction notes

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