Sulfuric Acid → 4-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamide

HRID 2091701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091701
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:12][C:13]=1[C:14]#[N:15].S(=O)(=O)(O)[OH:23]>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[S:12][C:13]=1[C:14]([NH2:15])=[O:23]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 592500334-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile

Produkt 1

HCID 592500274-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamideAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-(2,4-dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carbonitrile (30 mg, 0.088 mmol) was dissolved in sulfuric acid (0.200 mL, 3.75 mmol) and the mixture was stirred at rt for 1 hour. Water (1 mL) was added and the mixture was quenched with an excess of saturated NaHCO3. Precipitate was filtered off, washed with water and dried to afford the title compound (27 mg, 80%). LCMS: (FA) ES+, 358. 1H NMR (400 MHz, d6-DMSO) δ: 7.67 (d, 1H), 7.47 (d, 1H), 7.43 (dd, 1H), 3.72-3.69 (m, 4H), 3.44-3.42 (m, 4H).

Aufarbeitung

  1. customthe mixture was quenched with an excess of saturated NaHCO3
  2. filtrationPrecipitate was filtered off
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9089385f746743caaaf5aacd1483a051
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440664B2

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