Diazald → HCID 15029352, compound

HRID 249192

Reaction equation

HRID 249192 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 15029352HCID 15029352, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-89dfff02494f47cea89400c7958839d0
Source dataset
uspto-grants-1993_05
Patent number
US05213607

Linked notes

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