Dimethylamine → Ethyl 2-(dimethylamino)-4-(trifluoromethyl)-5-oxazolecarboxylate

HRID 359273ノート

反応式

HRID 359273 の反応式
[N+](C1C=CC(O)=CC=1)([O-])=O.[CH3:11][NH:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].Cl[C:21]1[O:22][C:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=1>CN(C)C=O>[CH3:11][N:12]([CH3:13])[C:21]1[O:22][C:23]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=1

参加物

6

反応物 4

HCID 674DimethylamineHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 12785855Ethyl 2-chloro-4-(trifluoromethyl)oxazole-5-carboxylate

生成物 1

HCID 20064719Ethyl 2-(dimethylamino)-4-(trifluoromethyl)-5-oxazolecarboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A reaction vessel was charged with 4.17 g (0.03 mol) of para-nitrophenol, 50 ml of dry dimethylformamide containing dimethylamine as impurity, and potassium carbonate. After stirring of this mixture at ambient temperature, there was added 4.86 g (0.02 mol) of ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate. The reaction mixture was stirred at ambient temperature for 24 hours. The resulting yellow mixture was extracted with ethyl ether and water. The organic phase was washed five times successively with 5% sodium hydroxide and five times with water, then dried with magnesium sulfate, and concentrated under reduced pressure to yield 2.2 g of a yellow solid which was recrystallized in methylcyclohexane to yield 1.7 g of a white powder. Chromatographic separation on silica gel using dichloroethane as eluent yielded 0.96 g of a light yellow powder product (m.p.=53°-55° C.) identified in Table I.

後処理

  1. stirringThe reaction mixture was stirred at ambient temperature for 24 hours
  2. extractionThe resulting yellow mixture was extracted with ethyl ether and water
  3. washThe organic phase was washed five times successively with 5% sodium hydroxide and five times with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-201f72462b354e109e110fdd195cfffd
出典データセット
uspto-grants-1991_03
特許番号
US05000775

反応ノート

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