Potassium Iodide → Ethyl 2-iodooxazole-4-carboxylate

HRID 508156ノート

反応式

HRID 508156 の反応式
N[C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:29].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.O>[I:29][C:2]1[O:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

参加物

9

反応物 6

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 86626551p-Toluenesulfonic acid dihydrate

生成物 1

HCID 46910517Ethyl 2-iodooxazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

2.00 g (12.81 mmol) of ethyl 2-amino-1,3-oxazole-4-carboxylate are added to a solution of 8.00 g (38.43 mmol) of p-toluenesulfonic acid dihydrate in 48 ml of acetonitrile. The suspension is cooled to 0° C., and a solution of 1.77 g (25.62 mmol) sodium nitrite and 5.32 g (32.02 mmol) potassium iodide in 7.2 ml of water is then added. The mixture is stirred at 0° C. for 10 min and, after warming to RT, further overnight. The mixture is then diluted with 200 ml of water. By addition of 1 M aqueous sodium bicarbonate solution, the pH is adjusted to 9. 24 ml of 2 M sodium thiosulfate solution are then added. The aqueous phase is extracted three times with in each case 30 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate. After filtration, the solvent is removed on a rotary evaporator. The residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 300:1→2:1).

後処理

  1. temperatureafter warming to RT, further overnight
  2. extractionThe aqueous phase is extracted three times with in each case 30 ml of ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent is removed on a rotary evaporator
  6. customThe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 300:1→2:1)

出典と根拠

ORDレコード
ord-36c047ae30d346b3a76d8801dcf3dc70
出典データセット
uspto-grants-2015_08
特許番号
US09095582B2

反応ノート

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