Hydrochloric Acid → HCID 70663362、化合物

HRID 878214ノート

反応式

HRID 878214 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6].[CH3:15][S-:16].[Na+].CCOC(C)=O.Cl>C1COCC1>[CH3:15][S:16][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)[C:5]([OH:7])=[O:6]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 112183892-Chloro-6-(trifluoromethyl)pyridine-4-carboxylic acid

生成物 1

HCID 70663362HCID 70663362、化合物収率 99.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a suspension of 2-chloro-6-(trifluoromethyl)isonicotinic acid (0.1 g, 443 μmol, prepared according to F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2004, 18, 3793-3798) in THF (5 mL) was added sodium thiomethoxide (155 mg, 2.22 mmol, CAS RN 50615-16-2) and the reaction mixture was heated to 70° C. (oil bath temperature) for 15 hours. After cooling down to room temperature, EtOAc (5 mL) and 1M aqueous HCl (2 mL) were added and the reaction mixture was stirred at room temperature for 30 min. The layers were separated and the aqueous layer was extracted with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give the desired compound as an off-white solid (0.105 g; 99%) which was used in the next step without further purification. MS (ESI): m/z=236.01 [M−H]−.

後処理

  1. temperatureAfter cooling down to room temperature
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-bc5e6b84f4ff4eb2b25a37d4c578c786
出典データセット
uspto-grants-2015_03
特許番号
US08987307B2

反応ノート

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