Sulfuric Acid → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine

HRID 335470

反応式

HRID 335470 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.[CH2:14]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH2:23][CH3:24])[C:17]=1[C:25](=[O:37])[C:26]([NH:28][N:29]=[CH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH3:15].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.O.NN.O>[CH2:14]([C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH2:23][CH3:24])[C:17]=1[C:25](=[O:37])[C:26]([N:28]([CH3:1])[N:29]=[CH:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:27])[CH3:15]

参加物

8

反応物 4

HCID 1118Sulfuric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 666919781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine

生成物 1

HCID 666915621-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine収率 79.7%

試薬・触媒・溶媒 3

HCID 24654Hydrazine hydrate (1:1)触媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

To a 50 mL volume three-necked flask, 7.6 mg of hydrazine hydrate, 2.3 ml of toluene, 629 mg of potassium carbonate and 574 mg of dimethyl sulfate were added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to 5° C. and 1.6 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine ((40-a)-(14)-6) solved in 2.3 g of toluene was added thereto. The reaction mixture was stirred at 5° C. for 31.5 hours. 5 mL of water was added and the resultant was neutralized to pH 7 with 20 wt % of sulfuric acid. The organic layer was removed and the aqueous layer was extracted with toluene two times. The organic layers were combined and concentrated under reduced pressure to give 1.22 g of a mixture (22:1 (GC area %)) of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine ((40-b)-(15)-5) and methyl 2-(2,6-diethyl-4-methylphenyl)-2-oxo-N-(phenylmethylidene)ethanehydrazonate (x-1).

後処理

  1. temperatureThe reaction mixture was cooled to 5° C.
  2. additionwas added
  3. stirringThe reaction mixture was stirred at 5° C. for 31.5 hours
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was extracted with toluene two times
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b48f21b2b5934cdab26d0199ff35063f
出典データセット
uspto-grants-2014_11
特許番号
US08884010B2

関連ノート

読み込み中…