Chloroform → HCID 282499, compound

HRID 429569Notes

Reaction equation

HRID 429569 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].C(Cl)(Cl)Cl.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](O)=O>>[C:17]([C:22]1[NH:11][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=2[N:10]=1)([CH3:21])([CH3:18])[CH3:16]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 6417Pivalic acidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 282499HCID 282499, compoundYield 77%

Procedure

A solution of 4-nitro-1,2-phenylenediamine (2.0 g, 13 mmol) in 10 ml of trimethylacetic acid was stirred at reflux for 12 h. Reaction mixture was concentrated in vacuo to yield a oil which was subjected to column chromatography (CHCl3, neat) to yield 2.2 g (10 mmol, 77%) of 2-tert-butyl-5-nitrobenzimidazole. The nitrobenzimidazole and 0.5 g of 10% Pd—C were dissolved in 100 ml of MeOH and stirred for 12 h under H2. The reaction mixture was filtered and concentrated in vacuo to provide 1.9 g (10 mmol, >95%) of the desired product.

Workup

  1. temperatureat reflux for 12 h
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. customto yield a oil which

Sources & evidence

ORD record
ord-01398acc4b554f40a830e08d95be3e5f
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

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