Sodium Hydroxide → HCID 178492290, compound

HRID 1583999Notes

Reaction equation

HRID 1583999 reaction equation
[OH-].[Na+].[SH:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:12][C:6]=2[N:5]=1.Cl.Cl[CH2:20][C:21]1[C:26]([CH3:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=1>C(O)C>[CH3:29][O:28][C:25]1[C:24]([CH3:30])=[CH:23][N:22]=[C:21]([CH2:20][S:3][C:4]2[NH:8][C:7]3[CH:9]=[CH:10][C:11]([O:13][C:14]([F:17])([F:15])[F:16])=[CH:12][C:6]=3[N:5]=2)[C:26]=1[CH3:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 178506357HCID 178506357, compound

Product 1

HCID 178492290HCID 178492290, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 ml of 4M sodium hydroxide solution are added dropwise to a mixture of 2.34 g of 2-mercapto-5-trifluromethoxy-1H-benzimidazole and 2.2 g of 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride in 50 ml of ethanol at room temperature and the mixture is stirred overnight at room temperature. The solvent is distilled off in vacuo, water is added, the mixture is extracted with ethyl acetate, the solution is dried and 4.3 g (95%) of the dihydrochloride of the title compound are precipitated with 4M hydrogen chloride in ether. The salt is dissolved in water and the base is precipitated with dilute sodium carbonate solution at pH 8 and recrystallized from diisopropyl ether. 3.0 g (78%) of the title compound of m.p. 152°-154° C. are obtained.

Workup

  1. distillationThe solvent is distilled off in vacuo, water
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate
  4. customthe solution is dried
  5. custom4.3 g (95%) of the dihydrochloride of the title compound are precipitated with 4M hydrogen chloride in ether
  6. dissolutionThe salt is dissolved in water
  7. customthe base is precipitated with dilute sodium carbonate solution at pH 8
  8. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e3e2899740034d2b85f014d4e8eb3013
Source dataset
uspto-grants-1985_11
Patent number
US04555518

Reaction notes

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