Sodium Hydroxide → 4-[1-(4-Cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoic acid

HRID 412445Notes

Reaction equation

HRID 412445 reaction equation
C[O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([S:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)=[O:25])[C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[CH:17]1([C:14]2[CH:13]=[CH:12][C:11]([CH:10]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([S:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=3)=[O:25])[C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:38])=[O:2])=[CH:5][CH:6]=3)=[CH:16][CH:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 674831474-[1-(4-Cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoic acid methyl ester

Product 1

HCID 223111524-[1-(4-Cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoic acidYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[1-(4-Cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoic acid methyl ester (0.53 g, 0.98 mmol) was dissolved in ethanol (96%, 11 mL) and sodium hydroxide (4 N, 1.47 mL) was added. The mixture was stirred overnight. The reaction was concentrated to dryness and added water (15 mL) and acidified with hydrochloric acid (4 N, 1.6 mL) to pH 2-3 and extracted with ethyl acetate (25 mL). The aqueous phase was extracted once more with ethyl acetate (15 mL) and the combined organic phases were washed 3 times with water (10 mL), dried over magnesium sulphate, filtered and concentrated in vacuo. Crystallisation from ethyl acetate:n-heptane gave 0.34 g of 4-[1-(4-cyclohexylphenyl)-3-(4-trifluoromethylsulfanylphenyl)ureidomethyl]benzoic acid.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additionadded water (15 mL)
  3. extractionextracted with ethyl acetate (25 mL)
  4. extractionThe aqueous phase was extracted once more with ethyl acetate (15 mL)
  5. washthe combined organic phases were washed 3 times with water (10 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-c780a346173e464f939603ff7bef6ec6
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

Loading…