Bentazon → HCID 20334435, compound

HRID 1706782Notes

Reaction equation

HRID 1706782 reaction equation
[CH3:1][CH:2]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[NH:6][S:5]1(=[O:16])=[O:15])[CH3:3].CC(C)([O-])C.[K+].[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(#N)C>[CH3:3][CH:2]([N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([S:24]([CH3:23])(=[O:26])=[O:25])[S:5]1(=[O:16])=[O:15])[CH3:1]

Participants

5

Reactant 3

HCID 2328BentazonHCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 20334435HCID 20334435, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 200 ml of acetonitrile was added with stirring 24 g(0.1 mole) of 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide and 11.8 g (0.105 mole) of potassium t-butoxide. The resultant mixture was heated to reflux, cooled, and 8.0 ml (0.105 mole of methanesulfonyl chloride in 100 ml of acetonitrile was added dropwise over a 0.5 hr period. The mixture was stirred 64 hours, filtered, and the solvent removed from the filtrate in vacuo. The crude product, 31.5 g, was washed with 2-50 ml-portions of methanol to afford 18.8 g of analytically pure 3-(1-methylethyl)-1-methylsulfonyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. m.p. 156°-158° C.

Workup

  1. temperatureto reflux
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe solvent removed from the filtrate in vacuo
  5. washThe crude product, 31.5 g, was washed with 2-50 ml-portions of methanol

Sources & evidence

ORD record
ord-80395852b966467185b074beba4530ed
Source dataset
uspto-grants-1980_06
Patent number
US04208514

Reaction notes

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