Hydrochloric Acid → HCID 117600520、化合物
反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[F:27][C:28]([F:39])([F:38])[CH2:29][O:30][C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34].Cl>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([NH:34][C:33]1[CH:35]=[CH:36][CH:37]=[C:31]([O:30][CH2:29][C:28]([F:27])([F:38])[F:39])[CH:32]=1)=[O:6]参加物
反応条件
- 温度
- 23 °C
実験手順
Under nitrogen, to 2-chloro-6-nitrobenzoic acid (1.27 g, 6.28 mmol, 1.00 equiv) in CH2Cl2 (20 mL) at 23° C. was added oxalyl chloride (0.585 mL, 6.91 mmol, 1.10 equiv) and DMF (16 μL, 0.19 mmol, 3.0 mol %). After stirring for 1 hr at 23° C., the reaction mixture was cooled to 0° C. and triethylamine (2.63 mL, 18.8 mmol, 3.00 equiv) and 3-(2,2,2-trifluoroethoxy)aniline (1.20 g, 6.28 mmol, 1.00 equiv) were added. After stirring for 15 min at 0° C., 3N HCl aq (50 mL) was added. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×3.0 mL). The combined organic phases were washed with brine (3.0 mL) and dried (MgSO4). The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc to afford 965 mg of the title compound (41% yield).
後処理
- temperaturethe reaction mixture was cooled to 0° C.
- stirringAfter stirring for 15 min at 0° C.
- customThe phases were separated
- extractionthe aqueous phase was extracted with CH2Cl2 (3×3.0 mL)
- washThe combined organic phases were washed with brine (3.0 mL)
- dry with materialdried (MgSO4)
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc
出典と根拠
- ORDレコード
- ord-1eaca08c7d6743d7a71687ae851ebb56
- 出典データセット
- uspto-grants-2015_12
- 特許番号
- US09216985B2
反応ノート
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