Methyl 2,2,2-trichloroacetimidate → Benzimidazole, 2-trichloromethyl-

HRID 1259924Notes

Reaction equation

HRID 1259924 reaction equation
[2H][C:2]1[C:7]([2H])=[C:6]([NH2:9])[C:5]([NH2:10])=[C:4]([2H])[C:3]=1[2H].[Cl:13][C:14]([Cl:20])([Cl:19])[C:15](=N)OC>C(O)(=O)C>[Cl:13][C:14]([Cl:20])([Cl:19])[C:15]1[NH:10][C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][C:6]=2[N:9]=1

Participants

4

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 107729501,2-Diaminobenzene (D4, 98%)

Product 1

HCID 77133Benzimidazole, 2-trichloromethyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

O-Phenylenediamine (25 g) was dissolved in acetic acid (750 ml), and methyl 2,2,2-trichloroacetimidate (28.5 ml) was added dropwise over 15 min. After stirring at room temperature for 1 hr, the reaction mixture was concentrated to about 150 ml, and poured into water (1500 ml). The precipitated crystals were collected by filtration, washed with water (1000 ml) and suspended in toluene (500 ml). The solvent was evaporated under reduced pressure. The residue was again suspended in toluene (500 ml) and the solvent was evaporated under reduced pressure. The residue was dried under reduced pressure to give the object product (51.8 g).

Workup

  1. concentrationthe reaction mixture was concentrated to about 150 ml
  2. additionpoured into water (1500 ml)
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water (1000 ml)
  5. customThe solvent was evaporated under reduced pressure
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-1b92d7eaa3d54eec991db234ba3e5787
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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