Disilathiane, 1,1,1,3,3,3-hexamethyl- → 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbothioamide

HRID 420896

反応式

HRID 420896 の反応式
C[Si](C)(C)[S:3][Si](C)(C)C.C[O-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([Cl:24])[C:15]=1[N:25]1[C:29]([NH:30][CH3:31])=[C:28]([CH:32]2[S:36][CH2:35][CH2:34][S:33]2)[C:27]([C:37]#[N:38])=[N:26]1>CN(C)C=O.CCOCC.O>[Cl:24][C:16]1[CH:17]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:19]=[C:14]([Cl:13])[C:15]=1[N:25]1[C:29]([NH:30][CH3:31])=[C:28]([CH:32]2[S:33][CH2:34][CH2:35][S:36]2)[C:27]([C:37](=[S:3])[NH2:38])=[N:26]1

参加物

7

反応物 3

HCID 76920Disilathiane, 1,1,1,3,3,3-hexamethyl-HCID 10942334Sodium MethoxideHCID 231319151-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbonitrile

生成物 1

HCID 231319131-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbothioamide収率 55%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To 1,1,1,3,3,3-hexamethyldisilathiane (0.157 g, 0.9 mmol) in dimethylformamide (4 mL) was added sodium methoxide (0.049 g, 0.9 mmol) and the resulting mixture was sonicated to provide a homogeneous blue colored solution. This resulting solution was added to the solution of 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-5-(methylamino)-1H-pyrazole-3-carbonitrile (0.08 g, 0.2 mmol) in dimethylformamide (5 mL) at room temperature under nitrogen. This mixture was stirred at room temperature for one and half hour. It was then diluted with ether (30 mL) and water (30 mL). The layers were separated and the aqueous layer was extracted with ether. The ethereal layers were combined and washed twice with water (2×20 mL), dried (Na2SO4), and concentrated to provide a yellow solid. Upon chromatographic purification via silica gel eluting with heptane:ethyl acetate (4:1 to 2:1), a yellow solid (0.048 g, 55%) was obtained. 19F-NMR: −63.634.

後処理

  1. customthe resulting mixture was sonicated
  2. customto provide a homogeneous blue colored solution
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether
  5. washwashed twice with water (2×20 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto provide a yellow solid
  9. customUpon chromatographic purification via silica gel eluting with heptane:ethyl acetate (4:1 to 2:1)

出典と根拠

ORDレコード
ord-f8f2fcccba364f3b87683540c273c7ca
出典データセット
uspto-grants-2012_01
特許番号
US08097732B2

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