Formic Acid → 4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-benzimidazole

HRID 505529Notes

Reaction equation

HRID 505529 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=1[NH2:14].[CH:19](O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:5][C:6]1[C:7]2[N:14]=[CH:19][NH:13][C:8]=2[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 568337453-(3-Bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine

Product 1

HCID 684281464-(3-bromo-5-chlorophenoxy)-5-chloro-1H-benzimidazole

Procedure

A solution of 3-(3-bromo-5-chlorophenoxy)-4-chlorobenzene-1,2-diamine (400 mg, 1.149 mmol) in 90% formic acid (5 mL) was heated to 100° C. for 1 hour. This mixture was concentrated in vacuo and then partitioned between ethyl acetate (40 mL) and sat. aq. NaHCO3 (40 mL). The organic extract was dried over MgSO4, filtered and concentrated in vacuo to give the desired compound. LRMS (M+1)=358.7.

Workup

  1. concentrationThis mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate (40 mL) and sat. aq. NaHCO3 (40 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9316698e4d86454ba7d603be21381547
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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