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

반응식

HRID 420896 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f8f2fcccba364f3b87683540c273c7ca
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097732B2

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