Triethylamine → HCID 67041561、化合物

HRID 62718ノート

反応式

HRID 62718 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Br:12])[C:8]=1[O:9][CH2:10][CH3:11])[NH2:5].[CH2:13](N(CC)CC)C.ClC1C=C(N[C:30]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=2)=[O:31])C=C(Cl)C=1O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:30]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([O:38][CH3:13])=[O:37])=[CH:34][CH:33]=2)=[O:31])[CH:6]=[C:7]([Br:12])[C:8]=1[O:9][CH2:10][CH3:11]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 433516973,5-Dibromo-4-ethoxyanilineHCID 670418954-(3,5-Dichloro-4-hydroxyphenylcarbamoyl)benzoic acid

生成物 1

HCID 67041561HCID 67041561、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3,5-Dibromo-4-ethoxyaniline (2) (100 mg, 339 μmol) was dissolved in DCM (2.5 mL) and treated with triethylamine (143 μL, 1.02 mmol). 4-(Chlorocarbonyl)benzoic acid methyl ester (3) (135 mg, 678 μmol) was added in one portion and the resultant dark orange mixture was stirred at RT for 3 h then partitioned between EtOAc and aqueous 1M HCl. The organic layer was washed successively with saturated aqueous NaHCO3, water and brine. The organic layer was then dried over MgSO4, filtered and the solvent evaporated in vacuo. The residue was triturated from Et2O and filtered. The filtered solid was washed with methanol and the washings were concentrated in vacuo to provide methyl 4-(3,5-dibromo-4-ethoxyphenylcarbamoyl)benzoate (4) (141 mg, 73%) as a pale brown solid: m/z 456 [M−H]− (ES−).

後処理

  1. customthen partitioned between EtOAc and aqueous 1M HCl
  2. washThe organic layer was washed successively with saturated aqueous NaHCO3, water and brine
  3. dry with materialThe organic layer was then dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customThe residue was triturated from Et2O
  7. filtrationfiltered
  8. washThe filtered solid was washed with methanol
  9. concentrationthe washings were concentrated in vacuo

出典と根拠

ORDレコード
ord-29f88504e4be420283fd0b5c412dddbb
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

反応ノート

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