Acetone → P-Toluenesulfonylhydrazide

HRID 1200204Notes

Reaction equation

HRID 1200204 reaction equation
[N+:1](=[C:3]1[CH:8]=[CH:7][C:6](=[O:9])[CH:5]=[C:4]1[O:10][CH3:11])=[N-:2].C[O:13][C:14]1[CH:15]=[C:16](O)[CH:17]=[CH:18][CH:19]=1.N(S([O-])(=O)=O)([S:23]([O-:26])(=O)=[O:24])[O].[K+].[K+].[K].[CH3:34]C(C)=O>>[CH3:11][O:10][C:4]1[C:3](=[O:13])[CH:8]=[CH:7][C:6](=[O:9])[CH:5]=1.[C:19]1([CH3:34])[CH:18]=[CH:17][C:16]([S:23]([NH:1][NH2:2])(=[O:26])=[O:24])=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 90073-MethoxyphenolHCID 3032624Potassium nitrosodisulfonateHCID 5462222PotassiumHCID 178493426HCID 178493426, compound

Product 2

HCID 15303P-ToluenesulfonylhydrazideHCID 761462-Methoxy-1,4-benzoquinone

Procedure

Alternatively, 4-diazo-3-methoxy-2,5-cyclohexadien-1-one can be synthesized chemically. First, 2-methoxy-p-benzoquinone is synthesized by the addition of m-methoxyphenol in acetone to an aqueous solution of potassium nitrosodisulfonate and potassium monobasic phosphate. On treatment of 2-methoxy-p-benzoquinone with p-toluenesulfonhydrazide, the antibiotic is produced. Purification of the product from the reaction mixture is accomplished by chromatography on a silica gel column with chloroform:methanol (9:1, v/v).

Sources & evidence

ORD record
ord-3b68f114707e45808313849bbf536fe3
Source dataset
uspto-grants-1990_02
Patent number
US04904764

Reaction notes

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