Benzene → Ninhydrin

HRID 1031910Notes

Reaction equation

HRID 1031910 reaction equation
C(Cl)(Cl)Cl.CS(C)=[O:7].[C:9]([O:12]CC)(=[O:11])[CH3:10].[CH3:15][OH:16].[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O.C(O)C>[CH:17]1[CH:22]=[C:21]2[C:15]([C:9]([OH:11])([OH:12])[C:10](=[O:7])[C:20]2=[CH:19][CH:18]=1)=[O:16]

Participants

9

Reactant 5

HCID 241BenzeneHCID 679Dimethyl SulfoxideHCID 887MethanolHCID 6212ChloroformHCID 8857Ethyl Acetate

Product 1

HCID 10236Ninhydrin

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Each of the specific compounds referred to in Table I was soluble in benzene, chloroform, dimethyl sulfoxide, ethyl acetate, methanol and ethanol, but insoluble in n-hexane and water. They gave positive responses to Dragendorff and Rydon-Smith reagents, but negative responses to Erhlich, Sakaguchi and ninhydrin reagents. UV absorption maxima were observed at about 219, 242 and 317 nm in methanol and acidic methanol which shifted to about 221, 252, 293 and 342 nm in alkaline methanolic solution. The IR spectra of these compounds exhibited in common the presence of amide at 1660-1680 cm-1. The IR spectra for BU-3557B1 and BU-3557C4 showed an additional carbonyl absorption at 1705 cm-1 which is attributed to the ketone carbonyl group in the alkyl chain of R.

Sources & evidence

ORD record
ord-2155b7f019ff45579f8fe2cb38fdd57f
Source dataset
uspto-grants-1990_09
Patent number
US04956374

Reaction notes

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