Potassium Hydroxide → HCID 15546112, compound

HRID 1595309Notes

Reaction equation

HRID 1595309 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:33])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:17]3[CH:18]=[C:19]([C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[CH2:30][CH2:31][CH3:32])=[CH:8][CH:7]=1>CO>[C:22]([C:19]1[CH:20]=[CH:21][C:16]2[N:15]=[C:14]([CH2:30][CH2:31][CH3:32])[N:13]([CH2:12][C:9]3[CH:8]=[CH:7][C:6]([C:5]([OH:33])=[O:4])=[CH:11][CH:10]=3)[C:17]=2[CH:18]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15546116HCID 15546116, compound

Product 1

HCID 15546112HCID 15546112, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of potassium hydroxide (1.0 g in 10 mL of water) was added to a solution of 4-(6-benzoyl-2-propyl-benzoimidazol-1-ylmethyl)-benzoic acid methyl ester (1.0 g) in methanol (25 mL). The mixture was heated at reflux for a period of 3 hours. The reaction mixture was cooled to ambient temperature. The methanol was evaporated under vacuum. The residue was diluted with water (30 mL), then extracted with ethyl acetate (24 mL). The aqueous phase was acidified with 1N HCl. The precipitated solid was collected and air dried to afford the tide compound (0.6 g, 63% yield) as a white solid m.p. 295-296° C. Anal. Calcd. for C25H22N2O3: C, 75.36; H, 5.57; N, 7.03. Found: C, 75.03; H, 5.65; N, 6.86. Mass spectrum (PBEI; M+) mlz 398. 1H-NMR (DMSO-d6; 400 MHz): δ13.0 (br s, 1H), 7.91 (d, 2H), 7.82 (s, 1H), 7.72 (d, 1H), 7.58-7.64 (m, 4H), 7.47 (t, 2H), 7.18 (d, 2H), 5.67 (s, 2H), 2.88 (t, 2H), 1.78 (m, 2H), and 0.94 ppm (t, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for a period of 3 hours
  3. customThe methanol was evaporated under vacuum
  4. additionThe residue was diluted with water (30 mL)
  5. extractionextracted with ethyl acetate (24 mL)
  6. customThe precipitated solid was collected
  7. customair dried

Sources & evidence

ORD record
ord-1040ded23c2c46628c71bfbd9e4a1d07
Source dataset
uspto-grants-2001_09
Patent number
US06288100B1

Reaction notes

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