Sodium Hydroxide → 2-[2-(4-Methylpiperazin-1-yl)ethylthio] benzimidazole

HRID 703500Notes

Reaction equation

HRID 703500 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[OH-].[Na+].Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1>C(O)C>[CH3:23][N:20]1[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][S:1][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 221271121-(2-Chloroethyl)-4-methylpiperazine hydrochlorideHCID 178527775HCID 178527775, compound

Product 1

HCID 221503952-[2-(4-Methylpiperazin-1-yl)ethylthio] benzimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Grams 2.2 2-mercapto-1H-benzimidazol and 2.4 g NaOH were dissolved in 40 ml 90% ethyl alcohol, then 3.5 g 1-(2-chloroethyl)-4-methylpiperazine hydrochloride were added thereto. The reaction mixture was refluxed for 2 hours, the solid precipitate removed by filtration, the limpid solution evaporated to dryness and the residue dissolved in chloroform and washed with water. The organic phase was made anhydrous, then evaporated to dryness and the residue chromatographed on a column eluting with chloroform, methyl alcohol, cyclohexane, ammonium hydroxide (68:15:15:0.2). The fractions which contained the product, were collected together and evaporated to dryness and the residue which was triturated with isopropyl ether, gave 0.65 g 2-[2-(4-methylpiperazin-1-yl)ethylthio] benzimidazole melting at 93°-95° C. (with a slight decomposition).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. customthe solid precipitate removed by filtration
  3. customthe limpid solution evaporated to dryness
  4. dissolutionthe residue dissolved in chloroform
  5. washwashed with water
  6. customevaporated to dryness
  7. customthe residue chromatographed on a column
  8. washeluting with chloroform, methyl alcohol, cyclohexane, ammonium hydroxide (68:15:15:0.2)
  9. customwere collected together
  10. customevaporated to dryness
  11. customthe residue which was triturated with isopropyl ether

Sources & evidence

ORD record
ord-e2729036770f4c149f76fc15dc39b9c6
Source dataset
uspto-grants-1991_01
Patent number
US04983620

Reaction notes

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