Sodium Hydroxide → HCID 178468685, compound

HRID 1647160Notes

Reaction equation

HRID 1647160 reaction equation
[C:1]([C:6]1[CH:15]=[CH:14][C:9]2[NH:10][C:11]([SH:13])=[N:12][C:8]=2[CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].[OH-].[Na+].Cl.[CH3:19][O:20][C:21]1[C:22]([CH2:29]Cl)=[N:23][CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>O.C(O)C>[C:1]([C:6]1[CH:15]=[CH:14][C:9]2[NH:10][C:11]([S:13][CH2:29][C:22]3[C:21]([O:20][CH3:19])=[C:26]([O:27][CH3:28])[CH:25]=[CH:24][N:23]=3)=[N:12][C:8]=2[CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chlorideHCID 178468686HCID 178468686, compound

Product 1

HCID 178468685HCID 178468685, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

5-Carbethoxy-2-mercapto-1H-benzimidazole (2.0 g, 9 mmol) and NaOH (0.36 g, 9 mmol) in H2O (1 ml) were dissolved in ethanol (30 ml). 3,4-dimethoxy-2-chloromethylpyridine hydrochloride (≈6.6 mmol) as a crude material were added and the mixture was heated to boiling. NaOH (0.26 g, 6.6 mmol) in H2O (1 ml) was added and the reflux was continued for 6 hours. The solvent was evaporated off and the residue was diluted with methylene chloride and water. The organic phase was dried over Na2SO4 and the solvent removed under reduced pressure. Crystallizing from CH3CN gave the desired product (1.75 g, 71%).

Workup

  1. temperaturethe mixture was heated to boiling
  2. customThe solvent was evaporated off
  3. additionthe residue was diluted with methylene chloride and water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. customCrystallizing from CH3CN

Sources & evidence

ORD record
ord-3851d0dba86647408d62d61255778a81
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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