1,2-Dichloroethane → Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate

HRID 62721ノート

反応式

HRID 62721 の反応式
BrC1C=C(N[C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:14])C=C(Br)C=1OCC.C(Cl)CCl.[CH2:29]([O:31][C:32]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][C:35]([NH2:36])=[CH:34][C:33]=1[C:43]([F:46])([F:45])[F:44])[CH3:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:29]([O:31][C:32]1[C:33]([C:43]([F:44])([F:45])[F:46])=[CH:34][C:35]([NH:36][C:13]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[O:14])=[CH:37][C:38]=1[C:39]([F:40])([F:41])[F:42])[CH3:30]

参加物

7

反応物 3

HCID 111,2-DichloroethaneHCID 67041561HCID 67041561、化合物HCID 86666596HCID 86666596、化合物

生成物 1

HCID 86666597Methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate収率 28%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-(Methoxycarbonyl)benzoic acid (4) (246 mg, 1.37 mmol) was dissolved in DCM (15 mL) and treated with EDC (654 mg, 3.41 mmol) and DMAP (33 mg, 273 μmol). The resultant mixture was stirred at RT for 15 min. 4-Ethoxy-3,5-bis(trifluoromethyl)aniline (3) (360 mg, 1.32 mmol) was added and the resultant mixture was stirred at RT for 20 h. The mixture was diluted with EtOAc and washed three times with 1 M HCl and then three times with NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified by silica gel chromatography (10% EtAOc in isohexane) to afford methyl 4-(4-ethoxy-3,5-bis(trifluoromethyl)phenylcarbamoyl)benzoate (5) (150 mg, 28%): m/z 436 [M+H]+ (ES+).

後処理

  1. washwashed three times with 1 M HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by silica gel chromatography (10% EtAOc in isohexane)

出典と根拠

ORDレコード
ord-42b4bc701d9e4e08bbfe555360d54a48
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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