Hydrochloric Acid → HCID 178426600, Verbindung

HRID 1780582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1780582
[CH3:1][CH:2]([CH3:23])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=1[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19](C)(=O)=O)[N:14]=1)=[O:4].S.[K].O.Cl>C(O)C>[SH:19][C:15]1[N:14]=[C:13]([C:7]2[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=2[NH:5][C:3](=[O:4])[CH:2]([CH3:1])[CH3:23])[CH:18]=[CH:17][N:16]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 190470382-methyl-N-[4-methyl-2-[2-(methylsulfonyl)-4-pyrimidinyl]phenyl]propanamideHCID 86743134Potassium hydrogensulfide

Produkt 1

HCID 178426600HCID 178426600, VerbindungAusbeute 75,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3.3 g (0.01 mol) 2-methyl-N-[4-methyl-2-[2-(methylsulfonyl)-4-pyrimidinyl]phenyl]propanamide was dissolved in 35 mL absolute ethanol and 3 g potassium hydrogen sulfide was added to this solution with stirring. The reaction mixture was stirred overnight at room temperature. 50 mL water was added and the volume reduced under vacuum to 40 mL. An additional 40 mL water was added and the solution thus obtained was made acidic with concentrated hydrochloric acid. The yellow precipitate was collected by filtration, washed with a little water, then dissolved in 50 mL 1N sodium hydroxide and treated with charcoal. The charcoal was filtered off and the filtrate was made acidic with concentrated hydrochloric acid. The bright yellow precipitate was collected by filtration, washed with water, then dried in a vacuum oven to yield 2.18 g of N-[2-(2-mercapto-4-pyrimidyl)-4-methylphenyl]-2-methylpropanamide. 1H NMR (CDCl3): δ 1.21 (d,6H), 2.40 (s,3H), 2.75 (m,1H), 7.40-8.60 (5H), 11.4(s,1H,NH), 11.9(s,1H,SH).

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customthe solution thus obtained
  3. filtrationThe yellow precipitate was collected by filtration
  4. washwashed with a little water
  5. dissolutiondissolved in 50 mL 1N sodium hydroxide
  6. additiontreated with charcoal
  7. filtrationThe charcoal was filtered off
  8. filtrationThe bright yellow precipitate was collected by filtration
  9. washwashed with water
  10. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-b3562fdc0cd74c21b333b62129199d87
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05631206

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