Sulfuryl chloride → 2-Chloro-5-(trifluoromethyl)-1,3-benzothiazole

HRID 30890

반응식

HRID 30890 반응식
S(Cl)([Cl:4])(=O)=O.S[C:7]1[S:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:10]=2[N:11]=1>>[Cl:4][C:7]1[S:8][C:9]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:10]=2[N:11]=1

참가 물질

3

반응물 2

HCID 24648Sulfuryl chloride2회HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiol

생성물 1

HCID 219858492-Chloro-5-(trifluoromethyl)-1,3-benzothiazole수율 94%

실험 절차

Sulfuryl chloride (9.09 g, 67.33 mmol) was added with stirring to 2-mercapto-5-(trifluoromethyl)benzothiazole (2.64 g, 11.22 mmol) over a period of 5 minutes. The reaction mixture was then allowed to stand for approximately 1 h. Ice water was added to the reaction mixture with stirring to decompose the excess of sulfuryl chloride, and the product was then extracted with ethyl acetate. The organic layer was washed with water (3×) and brine, dried over anhydrous Na2SO4 and concentrated. The resulting solid was dissolved in EtOAc and filtered though a short silica-gel column, eluting with EtOAc, to give 2-chloro-5-(trifluoromethyl)benzothiazole (2.50 g, 94%). LC-MS m/z 238.0 (MH+), ret. time 2.55 min; 1H NMR (400 MHz, DMSO-d6) δ 7.81 (d, 1H), 8.38 (m, 2H).

후처리

  1. extractionthe product was then extracted with ethyl acetate
  2. washThe organic layer was washed with water (3×) and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. dissolutionThe resulting solid was dissolved in EtOAc
  6. filtrationfiltered though a short silica-gel column
  7. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-921fd12bd97a499788225f411c64e142
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423156B2

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