Dilithium Sulfide → Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate

HRID 395395

反応式

HRID 395395 の反応式
Br[C:2]1[C:3]([CH2:19][CH:20]([CH3:22])[CH3:21])=[C:4]([C:15]([O:17][CH3:18])=[O:16])[C:5]([CH:12]([F:14])[F:13])=[N:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[S-2:23].[Li+].[Li+]>CN(C=O)C.Cl>[F:13][CH:12]([F:14])[C:5]1[C:4]([C:15]([O:17][CH3:18])=[O:16])=[C:3]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:2]([SH:23])=[C:7]([C:8]([F:11])([F:10])[F:9])[N:6]=1

参加物

5

反応物 2

HCID 10290727Dilithium SulfideHCID 15117750HCID 15117750、化合物

生成物 1

HCID 9974711Methyl 2-(difluoromethyl)-4-isobutyl-5-mercapto-6-(trifluoromethyl)-3-pyridinecarboxylate収率 83%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 10.11 g (0.026 mol) of methyl 5-bromo-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate (example 122 of U.S. Pat. No. 5,019,153) in 75 mL dry DMF was added 1.42 g (0.031 mol) of lithium sulfide in one portion and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with 150 mL of 10% HCl solution and extracted with ether (3×100 mL). The combined extracts were washed with water, dried (MgSO4) and evaporated. The residue was purified by kugelrohr distillation (oven temperature 100-110° C., 1.5 torr) to give 7.35 g (83%) of product as a yellow-green oil:

後処理

  1. extractionextracted with ether (3×100 mL)
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. distillationThe residue was purified by kugelrohr distillation (oven temperature 100-110° C., 1.5 torr)

出典と根拠

ORDレコード
ord-fc674029862348c7a91cee5d89176191
出典データセット
uspto-grants-2003_08
特許番号
US06605624B1

関連ノート

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