Benzoyl chloride → 2,6-Diethyl-4-nitrophenylthiourea

HRID 329603

Reaktionsgleichung

Reaktionsgleichung von HRID 329603
[S-:1][C:2]#[N:3].[K+].C(Cl)(=O)C1C=CC=CC=1.[CH2:14]([C:16]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[C:19]([CH2:26][CH3:27])[C:17]=1[NH2:18])[CH3:15].[OH-].[Na+]>CC(C)=O.O.C(O)C>[CH2:26]([C:19]1[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=[C:16]([CH2:14][CH3:15])[C:17]=1[NH:18][C:2]([NH2:3])=[S:1])[CH3:27]

Komponenten

8

Edukt 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 516872Potassium thiocyanateHCID 81426772,6-Diethyl-4-nitroaniline

Produkt 1

HCID 538496572,6-Diethyl-4-nitrophenylthioureaAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To 2.34 g (24.1 mmol) of potassium thiocyanate in 30 ml of acetone was added 2.32 ml (20.0 mmol) of benzoyl chloride. The mixture was then refluxed for 15 min, cooled to r.t., and 3.16 g (16.3 mmol) of 2,6-diethyl-4-nitroaniline obtained from step C was added. The mixture was then refluxed for 15 min, cooled to r.t., and poured into 200 ml of ice-water. The precipitate was collected and washed with water, then dissolved in a solution comprising 0.70 g (18 mmol) of sodium hydroxide in 5 ml of water and 50 ml of ethanol. The solution was refluxed for 1 hr, cooled to r.t., poured into icewater, then the precipitate was collected, washed with water several times, and dried. The solids were then triturated with ethyl acetate to yield 2.44 g (59.2%) of product. NMR (CDCl3, d6 -DMSO):δ 1.30 (t, 6H), 2.74 (q, 4H), 6.9 (b, 2H), 7.98 (s, 2H), 9 (b, 1H).

Aufarbeitung

  1. temperatureThe mixture was then refluxed for 15 min
  2. temperatureThe mixture was then refluxed for 15 min
  3. temperaturecooled to r.t.
  4. customThe precipitate was collected
  5. washwashed with water
  6. temperatureThe solution was refluxed for 1 hr
  7. temperaturecooled to r.t.
  8. additionpoured into icewater
  9. customthe precipitate was collected
  10. washwashed with water several times
  11. customdried
  12. customThe solids were then triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e0d9d0f0845d47f9bdc2f5af4d61b2b2
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892871

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