2-(2-Oxopropyl)-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione → HCID 54363480, compound

HRID 1284536Notes

Reaction equation

P(=O)([O-])OC(CC)(CC)[C:4]#[N:5].[CH3:12][O-].[Na+].[CH2:15]([N:19]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[S:20]1(=[O:22])=[O:21])[C:16]([CH3:18])=O>CN(C)C=O>[O:21]=[S:20]1(=[O:22])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[C:29](=[O:30])[N:19]1[CH2:15][C:16]([CH3:12])=[CH:18][C:4]#[N:5]

Participants

Conditions

Temperature: 34 °C

Procedure

7.4 g (42 millimoles) of diethylcyanomethyl phosphonate and 6.8 g (38 millimoles) of 30% strength sodium methylate were simultaneously added dropwise to 10.0 g (42 millimoles) of N-acetonylsaccharin in 200 ml of dimethylformamide, while stirring thoroughly, the temperature increasing to 34° C. The reaction mixture was stirred for a further hour at room temperature, after which the contents of the flask were poured onto ice-water and extracted three times with methylene chloride, the organic phase was dried and evaporated down under reduced pressure, and the crude product was recrystallized from ethanol to give 2.5 g (23%) of 3-(2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylprop-1-ene of melting point 118°-121° C.

Workup

stirringThe reaction mixture was stirred for a further hour at room temperature
additionafter which the contents of the flask were poured onto ice-water
extractionextracted three times with methylene chloride
customthe organic phase was dried
customevaporated down under reduced pressure
customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record: ord-3d67d6dd9d604e17b71f9ab148832d65
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04563474

Reaction notes

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