Methanol → HCID 178443880, compound

HRID 1030578Notes

Reaction equation

HRID 1030578 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.[OH-:13].[Na+].[OH2:15].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C[OH:26]>>[OH2:2].[C:3]([OH:2])(=[O:26])[C:12]([OH:15])=[O:13].[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8]([S:10][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:9][C:5]=2[CH:4]=1.[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8]([S:10][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:9][C:5]=2[CH:4]=1.[OH2:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 81401-BromooctaneHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178488032HCID 178488032, compound

Product 1

HCID 178443880HCID 178443880, compound

Procedure

To a solution of 5-methoxy-2-mercaptobenzimidazole (2 16 g, 12 mmol) (Varima, R. S., J. Indian Chem. Soc. 62, 73 (1985)) in methanol (100 mL) and 2N NaOH/H2O (20 mmol) was added octyl bromide (2.65 g, 12 mmol). The solution was stirred at ambient temperature for 16 hours, evaporated, dissolved in CH2Cl2, washed with saturated NaHCO3, and dried over Na2SO4. Evaporation of the solvent and flash chromatography (Merck Kieselgel, 5% MeOH/CH2Cl2) gave 1.4 of the title compound as a free base. Conversion of 600 mg of the free base to its oxalate salt gave 540 mg of a white solid. m.p. 102°- 106° C. NMR (DMSO-d6)δ7.10(m,3H), 3.25(t,J=4 Hz,2H), 1.20(br, 15H).

Workup

  1. customevaporated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent and flash chromatography (Merck Kieselgel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f10e4bf1d67c4fd7b50c6574f1f313ad
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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