Formic Acid → 2-(6,7-difluoro-1H-benzimidazol-1-yl)ethanol

HRID 603102Notes

Reaction equation

HRID 603102 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][OH:11])=[C:6]([F:12])[C:5]([F:13])=[CH:4][CH:3]=1.[CH:14](O)=O>>[F:13][C:5]1[CH:4]=[CH:3][C:2]2[N:1]=[CH:14][N:8]([CH2:9][CH2:10][OH:11])[C:7]=2[C:6]=1[F:12]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 579390152-[(6-Amino-2,3-difluorophenyl)amino]ethanol

Product 1

HCID 579390212-(6,7-difluoro-1H-benzimidazol-1-yl)ethanol

Procedure

A solution of 2-[(6-amino-2,3-difluorophenyl)amino]ethanol in 100 ml of formic acid is heated at 100° C. for 2 hours. The reaction is concentrated to dryness, taken into 100 ml of 2 N NH3 in ethanol and stirred for 2.5 hrs. The reaction is concentrated and taken into ethyl acetate. The resulting precipitate is collected by filtration and rinsed with cold ethyl acetate. The mother liquor is concentrated and purified by silica gel flash chromatography using ethyl acetate/heptane. The combined yield is 3.2 g or 93% for two steps based on 3.8 g of 2-[(2,3-difluoro-6-nitrophenyl)amino]ethanol.

Workup

  1. concentrationThe reaction is concentrated to dryness
  2. concentrationThe reaction is concentrated
  3. filtrationThe resulting precipitate is collected by filtration
  4. washrinsed with cold ethyl acetate
  5. concentrationThe mother liquor is concentrated
  6. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-652de91df2234a8b8b17489283ed324e
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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