Carbofuran → Carbamic acid, methyl(phenylthio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

HRID 1973391

Reaktionsgleichung

Reaktionsgleichung von HRID 1973391
[CH3:1][C:2]1([CH3:16])[O:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:11][C:12]([NH:14][CH3:15])=[O:13])[CH2:3]1.[C:17]1([S:23]Cl)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:15][N:14]([S:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12](=[O:13])[O:11][C:8]1[C:9]2[O:10][C:2]([CH3:16])([CH3:1])[CH2:3][C:4]=2[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2566CarbofuranHCID 11008040Benzenesulfenyl chloride

Produkt 1

HCID 39690Carbamic acid, methyl(phenylthio)-, 2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 11 g of carbofuran in 50 ml of pyridine was added to 14.5 g of benzenesulfenyl chloride and the mixture was allowed to stand overnight at room temperature. The mixture was filtered, 250 ml of dry ether was added to the filtrate and the mixture refiltered. The filtrate was concentrated under reduced pressure. The residue was washed by stirring with 50 ml of water for one hour at room temperature. When the oily product was stirred with 200 ml of hexane, about 80% dissolved. The hexane solution was decanted, washed six times with water, then with saturated aqueous sodium chloride solution, then dried over sodium sulfate. The dried solution was concentrated under reduced pressure and the residue distilled to give a colorless liquid, b.p. 168°-174° at 0.005 mm. Redistillation gave 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (methyl)(phenylthio)carbamate, b.p. 168° at 0.005 mm, nD25 1.5758. This compound crystallized upon standing, m.p. 66°. The n.m.r. spectrum was consistent with the assigned structure.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. addition250 ml of dry ether was added to the filtrate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washThe residue was washed
  5. stirringWhen the oily product was stirred with 200 ml of hexane, about 80%
  6. dissolutiondissolved
  7. customThe hexane solution was decanted
  8. washwashed six times with water
  9. dry with materialwith saturated aqueous sodium chloride solution, then dried over sodium sulfate
  10. concentrationThe dried solution was concentrated under reduced pressure
  11. distillationthe residue distilled
  12. customto give a colorless liquid, b.p. 168°-174° at 0.005 mm
  13. distillationRedistillation

Quellen und Nachweise

ORD-Eintrag
ord-a4d55b8384d1492bb3bcfd3a151c2bce
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03997549

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