Water → HCID 20189595, compound

HRID 1789044Notes

Reaction equation

HRID 1789044 reaction equation
[F:1][C:2]1([F:15])[O:14][C:5]2=[CH:6][C:7]3[NH:11][C:10]([SH:12])=[N:9][C:8]=3[CH:13]=[C:4]2[O:3]1.Cl.Cl[CH:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][N:21]=1)[CH3:19].[OH-].[Na+].O>C(O)C>[F:15][C:2]1([F:1])[O:14][C:5]2=[CH:6][C:7]3[NH:11][C:10]([S:12][CH:18]([C:20]4[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][N:21]=4)[CH3:19])=[N:9][C:8]=3[CH:13]=[C:4]2[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 201895902-(1-Chloroethyl)-4-methoxy-pyridine hydrochlorideHCID 178506005HCID 178506005, compound

Product 1

HCID 20189595HCID 20189595, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4 g of 2,2-difluoro-5H-[1,3]-dioxolo[4,5-f]benzimidazole-6-thiol, 3.6 g of (±)-2-(1-chloroethyl)-4-methoxy-pyridine hydrochloride, 1.4 g of sodium hydroxide, 3 ml of water and 50 ml of ethanol are stirred for 4 h at 65° C. The reaction mixture is concentrated to dryness, the residue is dissolved in 100 ml of 2N hydrochloric acid, impurities are extracted by shaking with ethyl acetate, and the aqueous phase is adjusted with sodium hydroxide solution to pH 10 and extracted with ethyl acetate. The organic phase is dried and concentrated. Recrystallisation from toluene gives 4.3 g (80.5%) of the title compound of m.p. 173°-175° C.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. dissolutionthe residue is dissolved in 100 ml of 2N hydrochloric acid
  3. extractionimpurities are extracted
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. concentrationconcentrated
  7. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-dd4623601ad14987b7dfd26605bbc2f8
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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