Sodium hydride → HCID 178423918, compound

HRID 1368653Notes

Reaction equation

HRID 1368653 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]([CH2:9][CH2:10][OH:11])[N:7]=[C:6]([OH:12])[C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].[Cl-].[NH4+]>CN(C)C(=O)C>[NH2:3][C:4]1[N:8]([CH2:9][CH2:10][O:11][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[N:7]=[C:6]([OH:12])[C:5]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178423917HCID 178423917, compound

Product 1

HCID 178423918HCID 178423918, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (0.35 g, 60% suspension in mineral oil) was added in one portion to a stirred solution of 5-amino-1-(2-hydroxyethyl)-4-(4-methylphenyl)-1-H-pyrazol-3-ol(1.0 g) (Preparation 32) in anhydrous N,N-dimethylacetamide (20 ml) under a nitrogen atmosphere at room temperature. The initial effervescence observed subsided after 2-3 minutes and an orange/brown mixture resulted. After a further 7 minutes, tert-butyldimethylsilyl chloride (0.65 g) was added to the mixture in one portion and the reaction mixture was stirred at room temperature for 2 hours. Saturated aqueous ammonium chloride (50 ml) was added to the reaction mixture and the resulting aqueous medium was extracted with ethyl acetate (2×50 ml). The combined organic extracts were washed with water (40 ml), brine (40 ml) then dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallised from dichloromethane/hexane to give the title compound as a white solid (0.66 g). m.p. 193.5-195° C.

Workup

  1. customan orange/brown mixture resulted
  2. waitAfter a further 7 minutes
  3. extractionthe resulting aqueous medium was extracted with ethyl acetate (2×50 ml)
  4. washThe combined organic extracts were washed with water (40 ml), brine (40 ml)
  5. dry with materialthen dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-0c244b64a9ae4454ad5fdc25656b6b39
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

Loading…