Pyridine → HCID 178493326、化合物

HRID 1254932ノート

反応式

HRID 1254932 の反応式
[CH3:1][O:2][C:3]1[C:11]([S:12]([CH3:14])=[O:13])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[OH:19][C:20]1[N:21]([CH3:25])[N:22]=[CH:23][CH:24]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C(OCC)(=O)C.CCCCCCC.O>[OH:19][C:20]1[N:21]([CH3:25])[N:22]=[CH:23][C:24]=1[C:5]([C:4]1[CH:8]=[CH:9][C:10]([C:15]([F:18])([F:17])[F:16])=[C:11]([S:12]([CH3:14])=[O:13])[C:3]=1[O:2][CH3:1])=[O:7]

参加物

8

反応物 4

HCID 1049PyridineHCID 24386Thionyl Chloride2 回HCID 679801182-Methoxy-3-methylsulfinyl-4-trifluoromethylbenzoic acidHCID 178481816HCID 178481816、化合物

生成物 1

HCID 178493326HCID 178493326、化合物収率 88.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 8900Heptane溶媒

反応条件

温度
-10 °C

実験手順

3.0 g of 2-methoxy-3-methylsulfinyl-4-trifluoromethylbenzoic acid and 1.02 g of 3-hydroxy-2-methylpyrazole are suspended in 30 ml of ethyl acetate and 4.21 ml of pyridine under an inert atmosphere and cooled to −20° C. with stirring. 1.24 g of thionyl chloride are then slowly added dropwise such that the temperature always remains below −15° C. Following the complete addition of the thionyl chloride, the mixture is stirred for a further 20 minutes and warmed to −10° C. 10 ml of cold water are then added, and the mixture is warmed to 0° C. After adding 40 ml of heptane, the suspension is filtered and washed with 20 ml of heptane, 10 ml of water and again with 20 ml of heptane. Drying gives 3.32 g of (5-hydroxy-1-methyl-1H-pyrazol-4-yl)[2-methoxy-3-(methylsulfinyl)-4-(trifluoromethyl)phenyl]methanone (84% yield).

後処理

  1. stirringthe mixture is stirred for a further 20 minutes
  2. temperaturethe mixture is warmed to 0° C
  3. filtrationthe suspension is filtered
  4. washwashed with 20 ml of heptane, 10 ml of water and again with 20 ml of heptane
  5. customDrying

出典と根拠

ORDレコード
ord-72362cc050bd4bb2b7deaa3be768b314
出典データセット
uspto-grants-2013_06
特許番号
US08455657B2

反応ノート

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