Sodium hydride → HCID 21925384, compound

HRID 1243321Notes

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[O:14].[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[S:25](Cl)(=[O:27])=[O:26]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:25]([C:18]1[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:17]=1[O:16][CH3:15])(=[O:27])=[O:26])[C:8](=[O:13])[C:7]2=[O:14]

Participants

Conditions

Temperature: 20 °C

Procedure

0.5 g of 60% sodium hydride in oil is added to a mixture of 3.6 g of 5-chloro-1H-indole-2,3-dione in 20 ml of DMF, and the mixture is stirred for 30 minutes at 20° C. 4.8 g of 2,4-dimethoxybenzenesulphonyl chloride are then added and the mixture is stirred at 20° C. for 1 hour. The resulting mixture is concentrated under vacuum (1.3 Pa), the residue is extracted with EtOAc, the organic phase is washed with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is triturated in iso ether and the precipitate formed is filtered off by suction. 2.9 g of the expected product are obtained after crystallization from hot EtOAc, m.p.=194.5° C.

Workup

stirringthe mixture is stirred at 20° C. for 1 hour
concentrationThe resulting mixture is concentrated under vacuum (1.3 Pa)
extractionthe residue is extracted with EtOAc
washthe organic phase is washed with water
dry with materialdried over Na2SO4
customthe solvent is evaporated off under vacuum
customThe residue is triturated in iso ether
customthe precipitate formed
filtrationis filtered off by suction

Sources & evidence

ORD record: ord-eef63851a0bf4a09a09bd46716f22d63
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119086B2

Reaction notes

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