3,5-Dimethylpyridine → Penoxsulam

HRID 1391845노트

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HRID 1391845 반응식
[NH2:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1.[F:15][CH:16]([F:33])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[C:20]=1[S:29](Cl)(=[O:31])=[O:30].N1C=C(C)C=C(C)C=1>CS(C)=O>[F:33][CH:16]([F:15])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[C:20]=1[S:29]([NH:1][C:2]1[N:10]=[C:9]2[N:4]([C:5]([O:13][CH3:14])=[N:6][CH:7]=[C:8]2[O:11][CH3:12])[N:3]=1)(=[O:30])=[O:31]

참가 물질

5

반응물 3

HCID 115653,5-DimethylpyridineHCID 114468885,8-Dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin-2-amineHCID 160503082-(2,2-Difluoroethoxy)-6-(trifluoromethyl)benzene-1-sulfonyl chloride

생성물 1

HCID 11784975Penoxsulam수율 93.1%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide촉매

실험 절차

2-Amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine (7.8 g, 0.040 mol) and 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride (13 g, 0.040 mol) were combined in 3,5-lutidine (31 g, 0.29 mol, 7.2 eq). The slurry was treated with methyl sulfoxide (0.040 g, 0.0005 mol, 0.012 eq) and stirred at ambient conditions for 8.5 hours. The reaction slurry was filtered, and the wet cake solids were slurried in a mixture of 15% sulfuric acid (80 mL) and acetonitrile (20 mL). The mixture was stirred for 25 minutes, then filtered, and the solids washed with water. After drying under vacuum at 55° C., 18 g of product was obtained as a white solid assaying at 97.4 wt % (91% yield).

후처리

  1. filtrationThe reaction slurry was filtered
  2. additionthe wet cake solids were slurried in a mixture of 15% sulfuric acid (80 mL) and acetonitrile (20 mL)
  3. stirringThe mixture was stirred for 25 minutes
  4. filtrationfiltered
  5. washthe solids washed with water
  6. customAfter drying under vacuum at 55° C.

출처 및 근거

ORD 기록
ord-a80a7b96a6d543f8a45591549157c42c
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07339058B2

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