2-sec-Butylphenol → Fenobucarb

HRID 1290268

Reaktionsgleichung

Reaktionsgleichung von HRID 1290268
[CH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH2:3][CH3:4])[CH3:2].CCN(CC)CC.[CH3:19][NH:20][C:21](=S)[OH:22]>C(#N)C>[CH3:19][NH:20][C:21](=[O:22])[O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:1]([CH2:3][CH3:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 69842-sec-ButylphenolHCID 8471TriethylamineHCID 178486072HCID 178486072, Verbindung

Produkt 1

HCID 19588Fenobucarb

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-Sec. butylphenol (1.5 g, 0.01 mole) 0.2 ml of Et3N was added under stirring. S-methyl ester of N-methylcarbamothioic acid (1.05 g, 0.01 mole) in acetonitrile (10 ml) was added dropwise over a period of 4 hrs, keeping reflux temperature. After 30 hr, acetonitrile was evaporated under vacuum. The residue was taken in dichloromethane (25 ml), washed with water and a 5% cold NaOH solution, followed by water and brine and dried over sodium sulphate. After removal of the solvent, the liquid residue obtained was further purified by distillation to give 2-Sec. butylphenyl N-methylcarbamate of the formula VI; IR: 3329 (N-H), 1730 (-COO), 1535, 1490 and 750 (aromatic); PMR (CdCl3, 90 MHz): 0.81 (3H, 1, primary methyl of side chain), 1.18 (3H, d, J=7Hz, secondary/methyl of side chain), 1.58 (2H, m, methylene protons of side chain), 2.88 (4H, doublet overlapping a multiplet, NH- CH3 and benzylic proton), 4.97 (1H, br s, N H) and 6.95 to 7.25 (4H, m, aromatic).

Aufarbeitung

  1. temperaturekeeping reflux temperature
  2. customacetonitrile was evaporated under vacuum
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customAfter removal of the solvent
  6. customthe liquid residue obtained
  7. distillationwas further purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-739590c798c34a58ab9698f27b114ff4
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750757

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