2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-methyl-N-(3,4,5-trimethoxyphenyl)-1H-indole-5-sulfonamide

HRID 50121Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH2:21][CH2:20]3)(=[O:16])=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1COCC1>[CH3:26][N:22]1[C:23]2[C:19](=[CH:18][C:17]([S:14]([NH:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)(=[O:16])=[O:15])=[CH:25][CH:24]=2)[CH:20]=[CH:21]1

Participants

Conditions

Temperature: 25 °C

Procedure

A 0° C. slurry of N-(3,4,5-trimethoxyphenyl)-1-methylindoline-5-sulfonamide (11.3 g, 0.030 mol) in THF (130 mL) was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (7.15 g, 0.0315 mol), stirred for 4 hours, warmed to 25° C., and stirred for 10 hours. The mixture was concentrated to half of its original volume, diluted with methyl tert-butyl ether (70 mL), cooled to 0° C., stirred for 2 hours, and filtered. The resulting solid was washed with methyl tert-butyl ether (50 mL), dried, and recrystallized from acetonitrile and methyl tert-butyl ether to provide 9.2 g of the desired product (81%).

Workup

stirringstirred for 10 hours
concentrationThe mixture was concentrated to half of its original volume
additiondiluted with methyl tert-butyl ether (70 mL)
temperaturecooled to 0° C.
stirringstirred for 2 hours
filtrationfiltered
washThe resulting solid was washed with methyl tert-butyl ether (50 mL)
customdried
customrecrystallized from acetonitrile and methyl tert-butyl ether

Sources & evidence

ORD record: ord-db195cdd843245ed9d6fc3e048cc80dd
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06710185B2

Reaction notes

Loading…