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

HRID 1480667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1480667
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 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide (7.34 g, 25.8 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, 1H), 7.26 (s, 2H), 6.90 (bs, 2H), 6.30 (s, 1H), 2.06 (s, 6H), 2.02 (s, 3H).

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-1adf50eb8f8f4c9d89feb7dc6ea759dc
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409902B2

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