2-Aminothiazole → N'-(2-Thiazolyl)-N-methyl-N-phenylformamidine

HRID 5149

Reaktionsgleichung

Reaktionsgleichung von HRID 5149
[CH3:1][N:2]([CH:9]=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.[NH2:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1>C1(C)C=CC=CC=1.NC1SC=CN=1>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[N:16]=[CH:9][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 21552-AminothiazoleHCID 24813Phosphorus oxychlorideHCID 66737N-Methylformanilide

Produkt 1

HCID 53775884N'-(2-Thiazolyl)-N-methyl-N-phenylformamidineAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21552-AminothiazoleKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of N-methylformanilide (67.6 g; 0.50 mole), toluene (25 g) and 2-aminothiazole (2.0 g; 0.02 mole) was added phosphorus oxychloride (45.8 mL; 0.50 mole) over 15 minutes. The temperature was maintained below 45° C. during this addition. Stirring was continued for 10 minutes, after which time a hot solution of 2-aminothiazole (48.0 g; 0.48 mole) in toluene (250 g) was added at 60°-65° C. over 45 minutes. The reaction was allowed to cool to room temperature with stirring and was quenched by dropwise addition into a mixture of 30% sodium hydroxide (325 g) and ice (300 g). The organic phase was washed with a mixture of water (100 g), sodium chloride (10 g), and sodium bicarbonate (7.5 g), followed by a saturated solution of sodium chloride (125 g); the resultant organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 98.3 g of crude product. Vacuum distillation gave pure 1 (60.0 g; 55.3%) as a yellow oil: bp 177° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.72 (s, 1H), 7.4-6.9 (m, 7H), 3.50 (S, 3H); IR(neat) 3075, 2950, 1615, 1580, 1490, 1345, 1310, 1120; MS (m/e) 217 (M+, base).

Aufarbeitung

  1. temperatureThe temperature was maintained below 45° C. during this addition
  2. stirringwith stirring
  3. customwas quenched by dropwise addition into a mixture of 30% sodium hydroxide (325 g) and ice (300 g)
  4. washThe organic phase was washed with a mixture of water (100 g), sodium chloride (10 g), and sodium bicarbonate (7.5 g)
  5. dry with materialthe resultant organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1c5d6f3e9f13411cab9d4d7d0306d9c2
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243055

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