Sodium Hydroxide → HCID 67916129, compound

HRID 1030570Notes

Reaction equation

HRID 1030570 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[CH2:13](Cl)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16].[OH-].[Na+]>CN(C)C=O>[CH3:16]/[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:14]\[CH2:13][S:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 6372219Geranyl chlorideHCID 178527775HCID 178527775, compound

Product 1

HCID 67916129HCID 67916129, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (NaH) (0.69 g, 30 mmol) in dimethylformamide (DMF) (100 mL) was added 2-mercaptobenzimidazole (4.5 g, 10 mmol) in DMF (20 mL) at 0° C. under N2. To the resultant solution was added geranyl chloride (5.16 g, 10 mmol) over 30 minutes. The reaction was stirred for five hours at ambient temperature under N2 then treated with 2N NaOH and extracted with diethyl ether (Et2O). The Et2O extract was washed with saturated NaCl, concentrated in vacuo, dissolved in methylene chloride, and dried over Na2SO4. Recrystallization from Et2O gave white crystalline 2-[(3,7-dimethyl-2,6(E)-octadienyl)-thio]-1H-1,3-benzimidazole (3.15 g, 36.6%). m.p. 98°-100° C. NMR (CDCl3):δ7.4(m, 2H), 7.1(m, 2H) 5.3(t,J=8 Hz, 1H) 5.0(m 1H) , 3.90(d, J= 10 Hz, 2H , 2.00(m, 4H), 1.65(m, 9H).

Workup

  1. extractionextracted with diethyl ether (Et2O)
  2. extractionThe Et2O extract
  3. washwas washed with saturated NaCl
  4. concentrationconcentrated in vacuo
  5. dissolutiondissolved in methylene chloride
  6. dry with materialdried over Na2SO4
  7. customRecrystallization from Et2O

Sources & evidence

ORD record
ord-a799f18a373b48f39c2713ea503cb4b6
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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