1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)urea

HRID 2199619노트

반응식

HRID 2199619 반응식
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:11]=3[CH:10]=2)[O:3]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31]>O1CCCC1.C(OCC)(=O)C>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:18][C:16]2[CH:15]=[CH:14][C:12]3[S:13][C:9]([B:4]4[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:19])([CH3:1])[O:3]4)=[CH:10][C:11]=3[CH:17]=2)=[O:29])=[CH:23][C:22]=1[C:30]([F:31])([F:32])[F:33]

참가 물질

5

반응물 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 1254677282-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine

생성물 1

HCID 1317356921-(4-Chloro-3-(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)urea

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To the solution of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine (825 mg, 3 mmol, 1 eq) in anhydrous tetrahydrofuran (15 mL) was added 4-chloro-3-(trifluoromethyl)phenyl isocyanate (678.3 mg, 1 eq) and the reaction solution was stirred at room temperature under nitrogen atmosphere overnight. The reaction was then diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted and concentrated under reduced pressure. 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-yl)urea was obtained as slightly brown colored foam in vacuo in the amount of 1.5 g which was used directly without further purification.

후처리

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, and brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper clear solution was decanted
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f0a98bc16591492faa2543af9a7e9d5e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359336B2

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