Sulfuric Acid → o-(1-Hydroxy-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoic acid

HRID 249191

反応式

HRID 249191 の反応式
[OH-].[Na+].[CH3:3][C:4]([NH:12][C:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16](=[O:23])[O:15][N:14]=1)([CH:9]([CH3:11])[CH3:10])[C:5]([O:7]C)=O.[O:24]1CCCC1.S(=O)(=O)(O)O>O.C(Cl)Cl>[OH:15][N:14]1[C:5](=[O:7])[C:4]([CH:9]([CH3:11])[CH3:10])([CH3:3])[N:12]=[C:13]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([OH:23])=[O:24]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15029344Methyl 2,3-dimethyl-2-[(1-oxo-2,3-benzoxazin-4-yl)amino]butyrate

生成物 1

HCID 15029348o-(1-Hydroxy-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoic acid収率 76%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

Sodium hydroxide (0.58 g, 0.0145 mol) in water is added to a solution of methyl 2,3-dimethyl-2-[(1-oxo-2,3-benzoxazin-4-yl)amino]butyrate (2.0 g, 0.00689 mol) and tetrahydrofuran under a nitrogen atmosphere. The reaction mixture is stirred at 45° C. for 36 hours then at room temperature for 6 days. The reaction mixture is concentrated in vacuo to give an oil. The oil is dissolved into water. The aqueous solution is cooled with an ice-bath and concentrated sulfuric acid is added until a pH of about 1 is obtained then the solution is extracted with ethyl acetate. The combined ethyl acetate extracts are dried with anhydrous magnesium sulfate and concentrated in vacuo to give a pale yellow solid. The solid is added to boiling methylene chloride and after 2/3 of the methylene chloride has evaporated, the mixture is filtered to give the title compound as a white solid (1.44 g, 76%), mp 186°-188° C., identified by IR and NMR spectral analyses.

後処理

  1. waitat room temperature for 6 days
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customto give an oil
  4. temperatureThe aqueous solution is cooled with an ice-bath
  5. customis obtained
  6. extractionthe solution is extracted with ethyl acetate
  7. dry with materialThe combined ethyl acetate extracts are dried with anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a pale yellow solid
  10. additionThe solid is added
  11. customafter 2/3 of the methylene chloride has evaporated
  12. filtrationthe mixture is filtered

出典と根拠

ORDレコード
ord-5c9c10f345e74325880a95d36a3d3ac8
出典データセット
uspto-grants-1993_05
特許番号
US05213607

関連ノート

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