3,5-Dimethylpyridine → Penoxsulam

HRID 1391846ノート

反応式

HRID 1391846 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 11784975Penoxsulam収率 93.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide触媒

実験手順

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). The slurry was treated with DMSO (0.040 g, 0.012 eq) and stirred at ambient conditions for 8.5 hours, with a slight rise in temperature noted in the first hours resulting from a reaction exotherm. The reaction slurry was filtered, and the wet cake solids were transferred to a separate vessel and 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 wt % (90% yield).

後処理

  1. customresulting from a reaction exotherm
  2. filtrationThe reaction slurry was filtered
  3. customthe wet cake solids were transferred to a separate vessel
  4. additionslurried in a mixture of 15% sulfuric acid (80 mL) and acetonitrile (20 mL)
  5. stirringThe mixture was stirred for 25 minutes
  6. filtrationfiltered
  7. washthe solids washed with water
  8. customAfter drying under vacuum at 55° C.

出典と根拠

ORDレコード
ord-08e111d5f690456eb3cffb50cd7c946b
出典データセット
uspto-grants-2008_03
特許番号
US07339058B2

反応ノート

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