Thiourea → N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide

HRID 1465609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465609
Br[CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=1[CH3:16])=O.[NH2:17][C:18]([NH2:20])=[S:19]>CCO>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([C:5]2[C:10]([CH3:11])=[CH:9][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[CH:7][C:6]=2[CH3:16])[N:17]=1

Komponenten

4

Edukt 2

HCID 2723790ThioureaHCID 18788447N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide

Produkt 1

HCID 58442517N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamideAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide (7.34 g, 25.9 g mmol) and thiourea (1.97 g, 25.9 mmol) in 95% EtOH (36.9 mL) was heated at reflux for 120 min. The solution was concentrated and added with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL). The resultant precipitate was filtered and recrystallized in toluene (50 mL). The solids were filtered and dried under vacuum to give N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide (5.83 g) as yellow solids in 86% yield: 1H NMR (500 MHz, DMSO-d6) δ 9.80 (s, 1 H), 7.26 (s, 2 H), 6.90 (s, 2 H), 6.30 (s, 1 H), 2.06 (s, 6 H), 2.02 (s, 3 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 120 min
  3. concentrationThe solution was concentrated
  4. additionadded with water (100 mL) and saturated aqueous Na2CO3 (5.0 mL)
  5. filtrationThe resultant precipitate was filtered
  6. customrecrystallized in toluene (50 mL)
  7. filtrationThe solids were filtered
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-647ea89b6969400d8365a4a1ed32899b
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999983B2

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