Water → HCID 10490994、化合物

HRID 2111453ノート

反応式

HRID 2111453 の反応式
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[F:6][C:7]1[C:12]([CH:13]=[O:14])=[C:11]([F:15])[C:10]([F:16])=[C:9](F)[C:8]=1[F:18].C(Cl)(=O)C.O>CC(N(C)C)=O>[F:6][C:7]1[C:8]([F:18])=[C:9]([S:3][C:1](=[O:4])[CH3:2])[C:10]([F:16])=[C:11]([F:15])[C:12]=1[CH:13]=[O:14]

参加物

6

反応物 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 69558PentafluorobenzaldehydeHCID 23670855Potassium ethanethioate

生成物 1

HCID 10490994HCID 10490994、化合物収率 69%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

Potassium thioacetate (1.28 g, 11.2 mmol) was added to a solution of pentafluorobenzaldehyde (1.24 mL, 10.2 mmol) in anhydrous DMA (20 mL). After a strong exotherm subsided, the mixture was stirred at rt for 30 min. Acetyl chloride (1.60 mL, 22.4 mmol) was added and the mixture was stirred for another 30 min, then poured into water and extracted twice with ethyl ether. The combined organic extracts were dried (Na2SO4) and evaporated to obtain an orange oil which was chromatographed (silica, CH2Cl2/hexanes, 2:3) affording a pale-yellow solid. Recrystallization from heptane gave white crystals (1.77 g, 69%). mp 86-87° C.; 1H NMR δ 2.53 (s, 3H), 10.30 (s, 1H); 13C NMR δ 30.9, 115.5, 117.2, 145.3, 148.7, 182.9, 187.9; FAB-MS obsd 252.9936, calcd exact mass 252.9946; Anal. Calcd. for C9H4F4O2S: C, 42.86; H, 1.60; S, 12.72. Found: C, 43.00; H, 1.71; S, 12.67.

後処理

  1. stirringthe mixture was stirred for another 30 min
  2. extractionextracted twice with ethyl ether
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customevaporated
  5. customto obtain an orange oil which
  6. customwas chromatographed (silica, CH2Cl2/hexanes, 2:3)
  7. customaffording a pale-yellow solid
  8. customRecrystallization from heptane

出典と根拠

ORDレコード
ord-a8bda83b898c40b08e8f4ee7a8af8b39
出典データセット
uspto-grants-2009_04
特許番号
US07518905B2

反応ノート

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