Dimethylamine → N,N-Dimethyl-2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonamide

HRID 571267Notes

Reaction equation

[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.C[CH2:17][N:18](C(C)C)[CH:19](C)C.CNC>C1COCC1>[CH3:17][N:18]([CH3:19])[S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 2,3-dioxoindoline-5-sulfonyl chloride (0.800 g, 3.26 mmol) in dry THF (10 ml), cooled at 0° C. under nitrogen, DIPEA (1.138 ml, 6.51 mmol) and dimethylamine 2M in THF (2.117 ml, 4.23 mmol) were added, and the mixture was allowed to stir at room temperature for 2.5 hours. The mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give N,N-dimethyl-2,3-dioxoindoline-5-sulfonamide (0.639 g, 2.51 mmol, 77% yield). MS/ESI+ 254.9 [MH]+.

Workup

customThe mixture was partitioned between ethyl acetate and water
extractionthe aqueous layer was extracted three times with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-bf7c9b58cb7441d083b60ae881df3368
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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