Bentazon → HCID 20334433, compound

HRID 1706780Notes

Reaction equation

HRID 1706780 reaction equation
[K].[CH3:2][CH:3]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[NH:7][S:6]1(=[O:17])=[O:16])[CH3:4].[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21]>C(#N)C>[CH3:4][CH:3]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[N:7]([C:20](=[O:21])[C:19]([CH3:24])([CH3:23])[CH3:18])[S:6]1(=[O:17])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 2328BentazonHCID 62493Pivaloyl chlorideHCID 5462222Potassium

Product 1

HCID 20334433HCID 20334433, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To 100 ml of acetonitrile was added 11.6 g of the potassium salt of 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. To the resultant stirred mixture was added dropwise 5.4 ml of trimethylacetyl chloride in 50 ml of acetonitrile over a 0.5 hour period. The resultant mixture was heated at 38°-40° C. for 22 hours, cooled, filtered and the solvent removed from the filtrate in vacuo. The residue was dissolved in 100 ml of ether and extracted with 100 ml of 5% potassium carbonate. The ether layer was washed once with 100 ml of water, dried with magnesium sulfate and filtered. The solvent was removed from the filtrate in vacuo and the solid residue, 8.3 g, extracted with 3-10 ml-portions of methanol. The resultant precipitate was air dried to afford 4.5 g of 3-(1-methylethyl)-1-(2,2-dimethyl-1-oxopropyl)-1H- -2,1,3-benzothiadiazin-4 (3H)-one-2,2-dioxide, m.p. 97.5°-99.5° C.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customthe solvent removed from the filtrate in vacuo
  4. dissolutionThe residue was dissolved in 100 ml of ether
  5. extractionextracted with 100 ml of 5% potassium carbonate
  6. washThe ether layer was washed once with 100 ml of water
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed from the filtrate in vacuo
  10. extractionthe solid residue, 8.3 g, extracted with 3-10 ml-portions of methanol
  11. customdried

Sources & evidence

ORD record
ord-858a0ee1602147fabf61c2566a357f27
Source dataset
uspto-grants-1980_06
Patent number
US04208514

Reaction notes

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