2-Chloro-6-methylaniline → N-(2-Chloro-6-methylphenyl)-4,6-dimethylpyrimidine-2-sulfonamide

HRID 34250

Reaktionsgleichung

Reaktionsgleichung von HRID 34250
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C([Li])CCC.[CH3:15][C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([S:23](F)(=[O:25])=[O:24])[N:17]=1>C(COC)OC>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][S:23]([C:18]1[N:17]=[C:16]([CH3:15])[CH:21]=[C:20]([CH3:22])[N:19]=1)(=[O:24])=[O:25]

Komponenten

5

Edukt 3

HCID 68972-Chloro-6-methylanilineHCID 144047184,6-Dimethylpyrimidine-2-sulfonyl fluorideHCID 178418339Butyllithium

Produkt 1

HCID 14404700N-(2-Chloro-6-methylphenyl)-4,6-dimethylpyrimidine-2-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 2-chloro-6-methylaniline (0.5 g, 3.5 mmol) in dimethoxyethane (15 mL) cooled to 0° C. was added butyl lithium (2.2 mL, 3.5 mmol) and the mixture was allowed to stir for 15 minutes. Then 4,6-dimethyl-2-pyrimidinesulfonyl fluoride (0.66 g, 3.5 mmol), prepared according to Brown and Hoskins, J. Chem. Soc. Perkin 1, 522-527 (1972) was added. The mixture stirred with warming to 25° C. for 1 hour. The mixture was concentrated and the residue triturated with butyl chloride. The resultant solid was acidified with 1N HCl and the solid was filtered. The product was a yellow-brown solid, m.p. 215°-219° C. NMR (200 MHZ) D6 -Acetone: δ 8.2 (bs, 1H), 7.4 (s, 1H), 7.2 (bs, 3H), 2.5 (s, 6H) and 2.35 (s, 3H).

Aufarbeitung

  1. additionPerkin 1, 522-527 (1972) was added
  2. stirringThe mixture stirred
  3. concentrationThe mixture was concentrated
  4. customthe residue triturated with butyl chloride
  5. filtrationthe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-cb50e60a73a34c928cefa1389b399c31
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04761173

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