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Trifluoroacetic acid → 5-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

HRID 871002
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HRID 871002 반응식
[Cl:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[S:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:5]2[S:4][N:3]=[C:2]([Cl:1])[C:6]=2[C:7]#[N:8])=[CH:14][CH:13]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86689222tert-Butyl 4-(3-chloro-4-cyanoisothiazol-5-yl)phenylcarbamate

생성물 1

HCID 866892235-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-Butyl 4-(3-chloro-4-cyanoisothiazol-5-yl)phenylcarbamate (4.76 g, 13.38 mmol) in DCM (100 ml) was treated with 10 mL of TFA. The reaction mixture was stirred at RT overnight. Solvent was removed in vacuo. The residue was diluted with water and DCM (100 ml). Layers were separated and the aqueous layer was extracted with DCM×2. The combined organics was washed with brine and dried with MgSO4, filtered, and concentrated. Product was rinsed with Et2O/hexanes and collected by filtration as a bright yellow solid (3.15 g, 94%).

후처리

  1. customSolvent was removed in vacuo
  2. additionThe residue was diluted with water and DCM (100 ml)
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with DCM×2
  5. washThe combined organics was washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washProduct was rinsed with Et2O/hexanes
  10. filtrationcollected by filtration as a bright yellow solid (3.15 g, 94%)

출처 및 근거

ORD 기록
ord-e139ca9805d64efcb72214d9a8de634b
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08969583B2

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