Acetone → (2,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]phenylthio)nitromethane

HRID 326791

Reaktionsgleichung

Reaktionsgleichung von HRID 326791
[BH4-].[Na+].CC(C)=O.[CH3:7][C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH:11]=[C:10]([CH3:25])[C:9]=1[SH:26].Cl.[N+:28]([CH3:31])([O-:30])=[O:29]>C(O)C.O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:7][C:8]1[CH:13]=[C:12]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH:11]=[C:10]([CH3:25])[C:9]=1[S:26][CH2:31][N+:28]([O-:30])=[O:29]

Komponenten

9

Edukt 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 6375Nitromethane2×HCID 4311764Sodium borohydrideHCID 150159512,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]benzenethiol

Produkt 1

HCID 15015954(2,6-Dimethyl-4-[2-(2-methylphenyl)acetamido]phenylthio)nitromethaneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178511488HCID 178511488, VerbindungKatalysator2×HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

Sodium borohydride (0.24 g, 6.3 mM) was added in portions to a stirred suspension of 2,6-dimethyl-4-[2-(2-metbylphenyl)acetamidophenyl thiocyanate (0.5 g, 1.6 mM), in ethanol (20 mL). After 30 minutes, acetone (0.47 mL, 6.4 mM) was added to remove excess sodium borohydride and the mixture stirred for 10 minutes to give a clear yellow solution containing 2,6-dimethyl-4-[2-(2-methylphenyl)acetamido]benzenethiol. Nitromethane (0.09 mL, 1.6 mM) was then added followed, after 10 minutes, by a solution of potassium ferricyanide (0.53 g, 1.6 mM) in water (10 mL). Progress of the reaction was followed by standard thin layer chromatographic (tlc) analysis. After 1 hour, unreacted thiol remained and so further nitromethane (0.45 mL, 0.8 mM) and a solution of potassium ferricyanide (0.27 g, 0.8 mM) in water (5 mL) was added. After about a further 1 hour, thiol was no longer detectable by tlc analysis. Water (500 mL) was then added. The reaction mixture was acidified to pH4 with 2M HCl and extracted with ethyl acetate. The extracts were dried (MgSO4) and the solvent evaporated. The sticky, orange solid was triturated with ether. The orange filtrate was separated and the solid residue discarded. The filtrate was evaporated to give (2,6-dimethyl-4-[2-(2-methylphenyl)acetamido]phenylthio)nitromethane as an orange/brown solid, m.p. 152° C. (decomposition) in 20% yield and which was used without purification.

Aufarbeitung

  1. customto remove excess sodium borohydride
  2. customto give a clear yellow solution
  3. waitAfter 1 hour
  4. waitAfter about a further 1 hour
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts were dried (MgSO4)
  7. customthe solvent evaporated
  8. customThe sticky, orange solid was triturated with ether
  9. customThe orange filtrate was separated
  10. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f53912d5002d4d55aadeaedcc2bc3892
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270342

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