Sodium Hydroxide → 2-[6-(2-Chloro-4-methoxyphenoxy)-1-hexylthio]-benzimidazole

HRID 232102Notes

Reaction equation

HRID 232102 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][C:12]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]SC1SCC(=O)N=1.[OH-].[Na+]>CN(C=O)C>[Cl:11][C:12]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-oneHCID 178527775HCID 178527775, compound

Product 1

HCID 223940752-[6-(2-Chloro-4-methoxyphenoxy)-1-hexylthio]-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir at room temperature for four days 2.5 gms. 2-mercapto-benzimidazole, 2 gms. of the iodide prepared in Examples 2 and 3, 25 ml. DMF and 0.71 gm. sodium hydroxide in a reaction flask. Remove the solvent and partition with water/methylene chloride. Elute on a silica column with 100% methylene chloride then 50/50 ethylacetate/methylene chloride to obtain the title compound. MS: m/z 391 (M+) H1 -NMR-200 mHz-δH (CDCl3), 1.5-1.6 (4H,m), 1.7-1.9 (4H,m), 3.35 (2H,t,J 7Hz), 3.75 (3H,s) 3.95 (2H,t,J 6Hz), 6.7-7.0 (3H,m), 7.2-7.4 (4H,m), 7.65-7.75 (1H,m).

Workup

  1. customRemove the solvent
  2. custompartition with water/methylene chloride
  3. washElute on a silica column with 100% methylene chloride

Sources & evidence

ORD record
ord-158c291dd97e4cb19ee6d41583538d85
Source dataset
uspto-grants-1989_07
Patent number
US04851423

Reaction notes

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