Sodium Hydroxide → HCID 44271328, compound

HRID 1387633Notes

Reaction equation

HRID 1387633 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>OC(C)=O.O.[Cl-].[Ti+3].[Cl-].[Cl-]>[NH2:20][C:16]1[CH:15]=[C:14]([C:12]2[N:13]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=3)[NH:10][C:11]=2[C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44271334HCID 44271334, compound

Product 1

HCID 44271328HCID 44271328, compound

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of 0.161 g (0.41 mmol) of 2-(4-methylthiophenyl)-4-(3-nitrophenyl)-5-(4-pyridyl)-1H-imidazole [See Ex. 62 below] in 3.4 mL of HOAc-H2O (1:1) was treated with 1.81 mL (2.87 mmol) of 20% aqueous titanium (III) chloride in one single portion. The mixture was stirred at rt for 20 min, then made basic with 10% NaOH. The aqueous mixture was extracted with 95:5 CH2Cl2/MeOH. The organic extracts were washed with H2O and saturated NaCl. Evaporation of solvent in vacuo afforded a yellow solid which was filtered through a plug of silica gel, eluting with 90:10 CHCl3/MeOH. The title compound was isolated as a pale yellow solid (0.129 g, 78%): CIMS (NH3, m/z): 359.1 (M++H).

Workup

  1. extractionThe aqueous mixture was extracted with 95:5 CH2Cl2/MeOH
  2. washThe organic extracts were washed with H2O and saturated NaCl
  3. customEvaporation of solvent in vacuo
  4. customafforded a yellow solid which
  5. filtrationwas filtered through a plug of silica gel
  6. washeluting with 90:10 CHCl3/MeOH

Sources & evidence

ORD record
ord-8b7a1298ea7b47399c2b42dec9a26479
Source dataset
uspto-grants-2001_07
Patent number
US06268370B1

Reaction notes

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