Carbon Dioxide → 1-Benzylbenzimidazole-2-carboxylic acid

HRID 982026

Reaction equation

HRID 982026 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:22](=[O:24])=[O:23].O>O1CCCC1>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:22]([OH:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 5633471-Benzyl-1H-benzimidazoleHCID 178418339Butyllithium

Product 1

HCID 200688741-Benzylbenzimidazole-2-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2.08 g (10 mmol) of 1-benzylbenzimidazole in 200 ml of dry tetrahydrofuran was cooled under N2 atmosphere to -78° C. and treated with 8.0 ml (20 mmol) of n-butyllithium. The resulting solution was warmed to 0° C. for 0.5 h, recooled to -78° C., and poured into a mixture of excess dry ice in 200 ml of tetrahydrofuran. After being allowed to warm, the solution was treated with 200 ml of water, washed with ether, neutralized, and washed with ether. The aqueous layer was concentrated in vacuo, after which the residue was triturated with 2% methanol in chloroform and filtered. The filtrate was dried over MgSO4 and concentrated to give 2.01 g (80%) of the desired compound as a white powder. Mass spectrum: (M-OH)+ =235.

Workup

  1. customrecooled to -78° C.
  2. temperatureto warm
  3. washwashed with ether
  4. washneutralized, and washed with ether
  5. concentrationThe aqueous layer was concentrated in vacuo
  6. customafter which the residue was triturated with 2% methanol in chloroform
  7. filtrationfiltered
  8. dry with materialThe filtrate was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-750c5365c4094d608c2b9ce6794daa31
Source dataset
uspto-grants-1991_02
Patent number
US04994477

Linked notes

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