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Potassium Fluoride → 4-isopropyl-6-methoxy-2-[1-(2-pyrimidinyl)-3-(trifluoro methyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289853
ノート
印刷プレビュー

反応式

HRID 1289853 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[C:11]([OH:12])=[CH:10][C:9]([C:13]([F:16])([F:15])[F:14])=[N:8]1.[F-].[K+].Br[CH2:20][N:21]1[C:25](=[O:26])[C:24]2[C:27]([CH:33]([CH3:35])[CH3:34])=[CH:28][C:29]([O:31][CH3:32])=[CH:30][C:23]=2[S:22]1(=[O:37])=[O:36]>CN(C=O)C.[Cl-].[NH4+]>[CH:33]([C:27]1[C:24]2[C:25](=[O:26])[N:21]([CH2:20][O:12][C:11]3[N:7]([C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)[N:8]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:10]=3)[S:22](=[O:37])(=[O:36])[C:23]=2[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=1)([CH3:35])[CH3:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideHCID 178516161HCID 178516161、化合物

生成物 1

HCID 867525504-isopropyl-6-methoxy-2-[1-(2-pyrimidinyl)-3-(trifluoro methyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide収率 60%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 25517Ammonium Chloride溶媒

実験手順

A mixture of 1-(2-pyrimidinyl)-3-trifluoromethyl-5-hydroxypyrazole (314 mg; 1.37 mmol) and KF (132 mg; 2.3 mmol) in 8 ml of DMF was stirred under nitrogen at room temperature and then 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (400 mg, 1.14 mmol) was added. The reaction mixture was stirred at room temperature for 1.25 hours and diluted with cold saturated ammonium chloride solution. The mixture was extracted with ether (3×), the organic layer was dried over magnesium sulfate and then filtered and concentrated in vacuo. The yellow solid residue (495 mg) was dissolved in methylene chloride and was purified by column chromatography (silica gel; 20-40% ethyl acetate/hexane) and recrystallized from ether/hexane to afford 330 mg (60%) of 4-isopropyl-6-methoxy-2-[1-(2-pyrimidinyl)-3-(trifluoro methyl)pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =2-pyrimidinyl; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 133°-134.5° C.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for 1.25 hours
  2. extractionThe mixture was extracted with ether (3×)
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe yellow solid residue (495 mg) was dissolved in methylene chloride
  7. customwas purified by column chromatography (silica gel; 20-40% ethyl acetate/hexane)
  8. customrecrystallized from ether/hexane

出典と根拠

ORDレコード
ord-0a3406668d1945e3b8a9c3d88c9b3dda
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05750550

反応ノート

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