2-Aminobenzimidazole → HCID 178508174, compound

HRID 413752Notes

Reaction equation

HRID 413752 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].C1(C)C=CC(S(O[C@H:23]2[CH2:30][CH2:29][CH2:28][C@@H:27](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:26][CH2:25][CH2:24]2)(=O)=O)=CC=1>CN(C=O)C>[NH2:1][C:2]1[N:6]([C@H:23]2[CH2:24][CH2:25][CH2:26][C@@H:27]([N:3]3[C:4]4[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=4[N:6]=[C:2]3[NH2:1])[CH2:28][CH2:29][CH2:30]2)[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 136242-AminobenzimidazoleHCID 24758Sodium hydrideHCID 178427784HCID 178427784, compound

Product 1

HCID 178508174HCID 178508174, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a hot (60° C.) solution of 2-aminobenzimidazole (0.22 g; 1.65 mmol) in DMF (25 ml) was added sodium hydride (70 mg; 60% dispersion in mineral oil), and the mixture was stirred for 30 minutes prior to addition of cis-1,5-bis(p-toluenesulfonyloxy)cyclooctane. The resulting mixture was stirred at 100° C. for four days, cooled and filtered. The filtrate was diluted with water and the precipitate was filtered off, washed with water and dried to yield the desired product (9 mg).

Workup

  1. stirringThe resulting mixture was stirred at 100° C. for four days
  2. temperaturecooled
  3. filtrationfiltered
  4. additionThe filtrate was diluted with water
  5. filtrationthe precipitate was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9e18e9d2ed0f47d9a257f420c5335d47
Source dataset
uspto-grants-2003_05
Patent number
US06569880B2

Reaction notes

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