Benzyl Alcohol → Benzyl (5-tert-butyl-1,3-oxazol-2-yl)carbamate

HRID 1748330ノート

反応式

HRID 1748330 の反応式
[C:1]([C:5]1[O:9][C:8](C(NN)=O)=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[N:15]([O-])=O.[Na+].[C:19]([O-:22])(O)=[O:20].[Na+].[CH2:24](O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)C.C1(C)C(C)=CC=CC=1>[C:1]([C:5]1[O:9][C:8]([NH:15][C:19](=[O:20])[O:22][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 672369965-Tert-butyl-1,3-oxazole-2-carbohydrazide

生成物 1

HCID 14054539Benzyl (5-tert-butyl-1,3-oxazol-2-yl)carbamate収率 22%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 7237O-Xylene溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 5-tert-butyl-1,3-oxazole-2-carbohydrazide (15 g, 82 mmol) in diethyl ether (250 mL) at 0° C. are added 6N aqueous HCl solution (210 mL, 1.26 mol) and NaNO2 (9.6 g, 139 mmol) aqueous solution over a period of 15 min. The reaction mixture is stirred at 0° C. for 1 h and saturated NaHCO3 solution is added to quench the reaction. The mixture is extracted with diethyl ether (3×100 mL) and the ether layers are combined, washed with brine, dried (Na2SO4) and concentrated. The residue is diluted with xylene (70 mL) and benzyl alcohol (27 g, 246 mmol) is added. The reaction mixture is refluxed for another 3 h and the solvent is removed under vacuum. The residue is purified by flash column chromatography to afford the title compound (5.0 g, 22%).

後処理

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture is extracted with diethyl ether (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. additionis added
  8. temperatureThe reaction mixture is refluxed for another 3 h
  9. customthe solvent is removed under vacuum
  10. customThe residue is purified by flash column chromatography

出典と根拠

ORDレコード
ord-9bb490a49e3b4db294d1a6b8e0563a80
出典データセット
uspto-grants-2015_10
特許番号
US09150577B2

反応ノート

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