N-cyclopropylbenzene-1,2-diamine → 1-Cyclopropyl-2-methyl-1H-benzimidazole

HRID 2231243Notes

Reaction equation

HRID 2231243 reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH2:11])[CH2:3][CH2:2]1.[CH2:12](C(CC)(CC)C([O-])([O-])[O-])[CH3:13]>C(OCC)(=O)C>[CH:1]1([N:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:11]=[C:12]2[CH3:13])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10582926N-cyclopropylbenzene-1,2-diamineHCID 21875354Triethylorthoaceate

Product 1

HCID 212862831-Cyclopropyl-2-methyl-1H-benzimidazoleYield 94.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.71 g (0.0115 mole) of N-cyclopropyl-1,2-phenylenediamine and 2.12 ml (0.0115 mole) of triethylorthoacetate in 50 ml of ethyl acetate was heated to reflux for 2 hours. The solvent was removed and the residue partitioned between chloroform and water. The organic phase was separated, dried over sodium sulfate and concentrated to give 1.87 g of a brown oil.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe solvent was removed
  3. customthe residue partitioned between chloroform and water
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-675887b0d42e428d85ed6c177ce0e9ed
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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