Bentazon → 1-(2-chloroacetyl)-3-(1-methylethyl)--1H-2,1,3-benzothiadiazin-4 (3H)-one-2,2-dioxide

HRID 1706779

Reaktionsgleichung

Reaktionsgleichung von HRID 1706779
[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+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(#N)C>[Cl:23][CH2:24][C:25]([N:6]1[C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9](=[O:10])[N:4]([CH:2]([CH3:1])[CH3:3])[S:5]1(=[O:16])=[O:15])=[O:26]

Komponenten

5

Edukt 3

HCID 2328BentazonHCID 6577Chloroacetyl chlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 203344321-(2-chloroacetyl)-3-(1-methylethyl)--1H-2,1,3-benzothiadiazin-4 (3H)-one-2,2-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 100 ml of acetonitrile was added 10.0 g of 3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one- -2,2-dioxide and 4.9 g of potassium t-butoxide. The mixture was stirred vigorously and 3.3 ml of chloroacetyl chloride in 50 ml acetanitrile was added dropwise over a 0.5 hour period. The resultant mixture as stirred overnight, filtered and the solvent removed from the filtrate in vacuo. The residue was washed with carbon tetrachloride and filtered. The tan granular precipitate was dissolved in 50 ml of methylene chloride and 50 ml of carbon tetrachloride was added. The methylene chloride was removed under a nitrogen atmosphere and the resultant mixture was filtered. The precipitate was washed 5% aqueous potassium carbonate, filtered and the white flocculent precipitate air dried to afford 2.23 g of 1-(2-chloroacetyl)-3-(1-methylethyl)- -1H-2,1,3-benzothiadiazin-4 (3H)-one-2,2-dioxide, m.p. 133°-135° C.

Aufarbeitung

  1. filtrationfiltered
  2. customthe solvent removed from the filtrate in vacuo
  3. washThe residue was washed with carbon tetrachloride
  4. filtrationfiltered
  5. dissolutionThe tan granular precipitate was dissolved in 50 ml of methylene chloride
  6. addition50 ml of carbon tetrachloride was added
  7. customThe methylene chloride was removed under a nitrogen atmosphere
  8. filtrationthe resultant mixture was filtered
  9. washThe precipitate was washed 5% aqueous potassium carbonate
  10. filtrationfiltered
  11. customthe white flocculent precipitate air dried

Quellen und Nachweise

ORD-Eintrag
ord-fc14f0eb9e5741ebac892d99d9681697
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04208514

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