Sodium hydride → HCID 178504603, compound

HRID 730058Notes

Reaction equation

HRID 730058 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[NH:11][C:12](=[S:22])[NH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:7]=[CH:6][N:5]=1.Cl[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH3:33])=[O:32])=[CH:27][CH:26]=1>C1COCC1.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]2[NH:11][C:12]([S:22][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:33])=[O:32])=[CH:27][CH:26]=3)=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 108597274-(2-Chloropyridin-4-yl)-5-(4-fluorophenyl)-1,3-dihydroimidazole-2-thioneHCID 13969650p-Methylsulfinylbenzyl chloride

Product 1

HCID 178504603HCID 178504603, compound

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaH (55-65%; 0.1 g; about 2 mmol) was introduced into a solution of 24a (0.31 g; 1.0 mmol) in absolute THF (15 ml). The initial charge was stirred at room temperature for 5 min, and 4-methylsulfinylbenzyl chloride (3, 0.19 g; 1.0 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. The yellow-brown solution was diluted with H2O and neutralized with 10% strength citric acid. The THF was removed and the aqueous solution was extracted with ethyl acetate (2×). The combined organic extract was washed with saturated NaCl solution (2×), dried over Na2SO4 and concentrated. The solids residue was purified by column chromatography (SiO2 60, CH2Cl2/EtOH 9.5+0.5). M.p. 179° C.

Workup

  1. additionThe initial charge
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. customThe THF was removed
  4. extractionthe aqueous solution was extracted with ethyl acetate (2×)
  5. extractionThe combined organic extract
  6. washwas washed with saturated NaCl solution (2×)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe solids residue was purified by column chromatography (SiO2 60, CH2Cl2/EtOH 9.5+0.5)

Sources & evidence

ORD record
ord-2198b5fe4e25424894cd473c879597f0
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

Loading…