Diazald → HCID 15029352、化合物

HRID 973364

反応式

HRID 973364 の反応式
[OH-].[K+].[CH3:3]C1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[N+](=C)=[N-].[OH:20][N:21]1[C:25](=[O:26])[C:24]([CH:28]([CH3:30])[CH3:29])([CH3:27])[N:23]=[C:22]1[C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([OH:35])=[O:34]>C(OCC)(=O)C.C(O)C.CCOCC>[OH:20][N:21]1[C:25](=[O:26])[C:24]([CH:28]([CH3:30])[CH3:29])([CH3:27])[N:23]=[C:22]1[C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([O:35][CH3:3])=[O:34]

参加物

8

反応物 4

HCID 6628Diazald2 回HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 15029348o-(1-Hydroxy-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)benzoic acid

生成物 1

HCID 15029352HCID 15029352、化合物収率 26%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of potassium hydroxide (0.19 g, 0.00339 mol) and ethanol is added portionwise to a 0° C. mixture of Diazald® N-methyl-N-nitroso-p-toluenesulfonamide (0.73 g, 0.0034 mol) and ether. The mixture is kept in an ice-bath for 10 minutes then in an water bath for 10 minutes. The diazomethane is distilled into a mixture of o-(1-hydroxy-4-isopropyl-4-methyl-5-oxo-2-imi-dazolin-2-yl)benzoic acid (0.67 g, 0.00243 mol) and ethanol. After 45 minutes the reaction mixture is quenched with acetic acid and concentrated in vacuo to give an oil. The oil is dissolved into ethyl acetate, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield an off-white solid. The solid is chromatographed using silica gel and methylene chloride/ethyl acetate 3:1 as eluent to give the title compound as a white solid (0.18 g, 26%), mp 146°-150° C., identified by IR and NMR spectral analyses.

後処理

  1. waitin an water bath for 10 minutes
  2. customAfter 45 minutes the reaction mixture is quenched with acetic acid
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield an off-white solid
  8. customThe solid is chromatographed

出典と根拠

ORDレコード
ord-ccccce07ac934270a6cb5b1eb987a777
出典データセット
uspto-grants-1991_11
特許番号
US05062881

関連ノート

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