Water → HCID 24131310, compound

HRID 1723865Notes

Reaction equation

HRID 1723865 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:5]([OH:7])=[O:6].[CH3:19]OC(OC)OC.O>C(O)=O>[F:18][C:14]1[CH:13]=[C:12]([N:11]2[C:10]3[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=3[N:1]=[CH:19]2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9005Trimethyl orthoformateHCID 54887667HCID 54887667, compound

Product 1

HCID 24131310HCID 24131310, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 3-amino-4-(3-fluorophenylamino)benzoic acid (4.96 g, 20.1 mmol) in formic acid (40 mL) was charged with trimethylorthoformate (2.4 mL, 22.0 mmol) and heated at reflux for 3 h after which time the mixture was allowed to cool to rt and stir for 12 h. The reaction mixture was then poured into 150 mL of H2O and stirred for 20 min yielding a precipitate which was isolated by filtration to give 1-(3-fluorophenyl)-1H-benzimidazole-5-carboxylic acid as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ 12.88 (s, 1H), 8.73 (s, 1H), 8.32 (s, 1H), 7.95 (d, J=8.5 Hz, 1H), 7.75-7.66 (m, 3H), 7.59 (d, J=8.0 Hz, 2H), 7.38 (t, J=8.8 Hz, 1H); MS (ES+): m/z 257 [MH+].

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h after which time the mixture
  3. stirringstirred for 20 min
  4. customyielding a precipitate which
  5. customwas isolated by filtration

Sources & evidence

ORD record
ord-8b839f617f5c47f4a32915f0ceda34cb
Source dataset
uspto-grants-2009_02
Patent number
US07485658B2

Reaction notes

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