Dimethyl Sulfoxide → HCID 178482771, compound

HRID 2209816Notes

Reaction equation

HRID 2209816 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([OH:28])[CH3:27])=[CH:21][C:20]=3[CH2:29][NH:30][CH3:31])[CH2:15][CH2:14]2)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.FC(F)(F)C(O)=O.CS(C)=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=3[CH2:29][NH:30][CH3:31])[CH2:15][CH2:14]2)[CH3:12])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 178482772HCID 178482772, compound

Product 1

HCID 178482771HCID 178482771, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

285 mg (0,613 mMol) of trans-N-(4-chlorobenzene-sulphonyl)-N-methyl-4-[4-(2-hydroxypropyl)-methylaminomethylphenyl]cyclohexylamine are oxidised using the Pfitzner-Moffatt method (380 mg (1.94 mMol) of dicyclohexylcarbodiimide, 35 mg (0.3 mMol) of trifluoroaceticacid, 0.9 ml (12.8 mMol) of dimethylsulphoxide and 2 ml of benzene). 160 mg (56% of theory) of the title compound are obtained in the form of colourless crystals, melting point 98°-100° C. 1H-NMR spectrum (200 MHz, CDCl3); signals at ppm: 1.35 (m, 1H), 1.5-2.0 (m,9H), 2.15 (s,2H), 2.3 (s,2H), 2.4 (m, 1H) , 2.8 (s, 3H) , 3.15 (s,2H) , 3.55 (S, 2H) , 3.9 (m, 1H) , 7.1-7.7 (2q, 8H).

Sources & evidence

ORD record
ord-d7fd1ae752ec4e77a15d700296203a39
Source dataset
uspto-grants-1995_10
Patent number
US05455273

Reaction notes

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