4,5-Dichloro-1,2-phenylenediamine → 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

HRID 230400

Reaction equation

HRID 230400 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[F:11][C:12]([F:18])([F:17])[CH2:13][C:14](O)=O>Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[NH:9][C:14]([CH2:13][C:12]([F:18])([F:17])[F:11])=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 792974,5-Dichloro-1,2-phenylenediamine2×HCID 27779723,3,3-Trifluoropropionic acid

Product 1

HCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

To 4,5-dichloro-1,2-phenylenediamine (25 g) was added 3,3,3-trifluoropropionic acid (25 mls) and 4N HCl (90 mL). The resulting mixture was heated to 100° C. overnight. The reaction mixture was quenched with water, basicified with concentrated NH4OH, extracted with EtOAc, and dried over Na2SO4. The crude product was filtered through a plug of silica gel, eluting with 30% EtOAc/hexanes, and collecting the red band. The fractions were concentrated to yield a mixture of the desired title compound and 4,5-dichloro-1,2-phenylenediamine. The crude material was dissolved in small amount of CH2Cl2 and triturated with hexanes to yield the title compound as a tan solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationThe crude product was filtered through a plug of silica gel
  5. washeluting with 30% EtOAc/hexanes
  6. customcollecting the red band
  7. concentrationThe fractions were concentrated
  8. customto yield

Sources & evidence

ORD record
ord-23129c6ce93049ef924f893f54ad0ff8
Source dataset
uspto-grants-2009_07
Patent number
US07566733B2

Linked notes

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