Dimethylformamide → Benzimidazole

HRID 1280090Notes

Reaction equation

HRID 1280090 reaction equation
[C:1]1(Cl)[C:7](=O)[C:6](Cl)=[C:5](Cl)[C:3](=O)[C:2]=1Cl.C[N:14]1[C:18](=O)CCC1.C[N:21](C=O)C>>[N:21]1[C:2]2[CH:3]=[CH:5][CH:6]=[CH:7][C:1]=2[NH:14][CH:18]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 8371ChloranilHCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 5798Benzimidazole

Procedure

Each resin was suspended in DMF (200 μL) and a 1 M solution of the aldehyde in DMF was added (0.20 mmol, 200 μL), followed by a 0.25 M solution of chloranil in NMP (0.20 mmol, 800 μL). The resins were shaken for 18 h, the liquid was drained and the resins were washed successively with 1.2-mL portions of NMP (3×), 1 M DIEA/NMP (2×), NMP (3×), MeOH (3×) and DCM (4×). The reaction block was placed in a vacuum chamber for 30 min in order to dry the resin.

Workup

  1. washthe resins were washed successively with 1.2-mL portions of NMP (3×), 1 M DIEA/NMP (2×), NMP (3×), MeOH (3×) and DCM (4×)
  2. waitThe reaction block was placed in a vacuum chamber for 30 min in order
  3. customto dry the resin

Sources & evidence

ORD record
ord-6ecdd42ecc444b7cb38557f95ce4c42a
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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