Diethyl (cyanomethyl)phosphonate → 4-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylbut-1-ene

HRID 1284540Notes

Reaction equation

HRID 1284540 reaction equation
CCOP(OCC)(C[C:7]#[N:8])=O.[CH3:12][O-].[Na+].O=[C:16]([CH2:18][CH2:19][N:20]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:21]1(=[O:23])=[O:22])[CH3:17]>CN(C)C=O>[O:22]=[S:21]1(=[O:23])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=2[C:30](=[O:31])[N:20]1[CH2:19][CH2:18][C:16]([CH3:12])=[CH:17][C:7]#[N:8]

Participants

5

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 10942334Sodium MethoxideHCID 130591402-(3-Oxobutyl)-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

Product 1

HCID 542356344-(2,3-Dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylbut-1-eneYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.5 g (54 millimoles) of diethyl cyanomethyl phosphonate and 8.7 g (48 millimoles) of 30% strength sodium methylate were simultaneously added dropwise to 10.0 g (40 millimoles) of N-(2-oxobut-4-yl)-saccharin in 150 ml of absolute dimethylformamide, while stirring thoroughly. The reaction mixture was stirred for a further 5 hours at 40° C., after which the contents of the flask were poured onto ice-water, and the precipitated crystals were filtered off under suction and recrystallized from ethanol to give 2.2 g (20%) of 4-(2,3-dihydro-1,1-dioxido-3-oxo-1,2-benzisothiazol-2-yl)-1-cyano-2-methylbut-1-ene of melting point 117°-118° C.

Workup

  1. stirringThe reaction mixture was stirred for a further 5 hours at 40° C.
  2. additionafter which the contents of the flask were poured onto ice-water
  3. filtrationthe precipitated crystals were filtered off under suction
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-18060f55c34f4124a6f044bc8fba7f75
Source dataset
uspto-grants-1986_01
Patent number
US04563474

Reaction notes

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