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

HRID 9575

反応式

HRID 9575 の反応式
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

参加物

3

反応物 2

HCID 24648Sulfuryl chloride2 回HCID 1784190875-(trifluoromethyl)-1,3-benzothiazole-2-thiol

生成物 1

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

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d12c540085124d09aa48e1da1b1b4a13
出典データセット
uspto-grants-2006_08
特許番号
US07091228B2

関連ノート

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