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Hydrochloric Acid → N-methoxymethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide

HRID 644895
ノート
印刷プレビュー

反応式

HRID 644895 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][N:10]=[C:11]=[S:12].[C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=2)=[C:17]([C:28]([F:31])([F:30])[F:29])[CH:16]=1)#[N:14].Cl>C(OCC)(=O)C>[CH3:7][O:8][CH2:9][NH:10][C:11]([N:24]1[C:25]([CH3:27])=[CH:26][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][C:17]=2[C:28]([F:29])([F:30])[F:31])=[N:23]1)=[S:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 140624Methoxymethyl isothiocyanateHCID 178623343-(4-Cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole

生成物 1

HCID 17862473N-methoxymethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide収率 32.4%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

実験手順

Potassium carbonate (0.23 g, 1.7 mmol) and methoxymethyl isothiocyanate (0.15 g, 1.5 mmol) were added to a solution of 3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole (0.40 g, 1.5 mmol) in ethyl acetate (10 ml), and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10), to give a white solid of N-methoxymethyl-3-(4-cyano-2-trifluoromethylphenyloxy)-5-methylpyrazole-1-carbothioamide (0.18 g, yield: 32.4%) mp: 89-90° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.84 (s, 3H), 3.44 (s, 3H), 5.13 (d, J=6.2 Hz, 2H), 5.98 (m, 1H), 7.44 (d, J=8.7 Hz, 1H), 7.84 (dd, J=2.0 and 8.7 Hz, 1H), 8.01 (d, J=2.0 Hz, 1H), 8.95-9.30 (m, 1H).

後処理

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10)

出典と根拠

ORDレコード
ord-c5880e167f0a426a8ac8bad77878668a
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700786B2

反応ノート

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