Ethyl Acetate → 4-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acid

HRID 412427ノート

反応式

HRID 412427 の反応式
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([O:37][CH3:38])[CH:28]=2)=[O:25])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:6][CH:5]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[CH:17]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:30]=[C:29]([O:37][CH3:38])[CH:28]=2)=[O:25])[C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:39])=[O:2])=[CH:9][CH:8]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 697335134-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acid methyl ester

生成物 1

HCID 223111384-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acid収率 62.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-[1-(Cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acid methyl ester (3.0 g) was dissolved in absolute ethanol (50 mL), sodium hydroxide (4 N, 15 mL) was added and the reaction mixture was stirred at room temperature for 16 hours. The organic solvent was removed in vacuo, and additional water (50 mL) was added, pH was adjusted with hydrochloric acid (4 N) to acidic reaction and then ethyl acetate (200 mL) was added. The organic phase was washed with water (5×50 mL), dried (magnesium sulphate), filtered and evaporated in vacuo. The residue was recrystallised from acetonitrile (25 mL) to afford 4-[1-(cyclohexylphenyl)-3-(3-methoxy-5-trifluoromethylphenyl)ureidomethyl]benzoic acid (1.83 g) as crystals.

後処理

  1. customThe organic solvent was removed in vacuo, and additional water (50 mL)
  2. additionwas added
  3. custompH was adjusted with hydrochloric acid (4 N) to acidic reaction
  4. washThe organic phase was washed with water (5×50 mL)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was recrystallised from acetonitrile (25 mL)

出典と根拠

ORDレコード
ord-de192ed945b84cd58762e70fe3ca46e9
出典データセット
uspto-grants-2003_05
特許番号
US06562807B2

反応ノート

読み込み中…