Acetone → Anthrone

HRID 2049236Notes

Reaction equation

HRID 2049236 reaction equation
[H][H].C(O[C:6](=[O:8])[CH3:7])C.C(Cl)(Cl)Cl.[CH3:13][C:14]([CH3:16])=O.N1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O.CS(C)=O.CO.C(O)C>[CH:13]1[C:7]2[C:6](=[O:8])[C:22]3[C:21](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:20][C:19]=2[CH:18]=[CH:16][CH:14]=1

Participants

10

Reactant 5

HCID 180AcetoneHCID 1049PyridineHCID 6212ChloroformHCID 8857Ethyl AcetateHCID 178418361HCID 178418361, compound

Product 1

HCID 7018Anthrone

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

An amylase inhibitor, TAI-B; being a white amorphous powder; having a decomposition point at 169°-174° C.; containing carbon, hydrogen and nitrogen with the analytical values (%) of C: 42.20, H: 6.47, N: 2.08; having an optical rotatory value of [α]D20 =+142°(c=0.5%, water); having a pKa value of 4.5 (in water); being of molecular weight 650-700 as determined; being soluble in water and dimethylsulfoxide, slightly soluble in methanol and pyridine, and insoluble in ethanol, ethylacetate, chloroform or acetone; having the infrared absorption spectrum shown in FIG. 2; having the nuclear magnetic resonance spectrum shown in FIG. 4; giving positive reactions with Molisch and anthrone; its acid hydrolyzate giving a positive reaction with ninhydrin; and showing the Rf values on thin layer chromatography and paper chromatography as follows:

Workup

  1. customat 169°-174° C.
  2. customthe infrared absorption spectrum

Sources & evidence

ORD record
ord-33b4495bca9446ac8ace4d13e658d348
Source dataset
uspto-grants-1980_04
Patent number
US04197292

Reaction notes

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