Dimethyl Sulfide → HCID 21461371, compound

HRID 1941479Notes

Reaction equation

HRID 1941479 reaction equation
CSC.[N+:4]([C:7]1[CH:24]=[CH:23][C:10]([CH:11]=[N:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([O-:6])=[O:5].[C:25]1([CH:31]=[N+]=[N-])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.C(OC)(C)(C)C.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[N+:4]([C:7]1[CH:24]=[CH:23][C:10]([CH:11]2[CH:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:12]2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([O-:6])=[O:5]

Participants

7

Reactant 3

HCID 1068Dimethyl SulfideHCID 136601Benzene, (diazomethyl)-HCID 693818Benzenesulfonamide, 4-methyl-N-[(4-nitrophenyl)methylene]-

Product 1

HCID 21461371HCID 21461371, compound

Reagents, catalysts & solvents 3

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a stirred solution of dimethylsulphide (5 μl, 0.07 mmol), rhodium (II) acetate (2 mg, 0.005 mmol) and N-(4-nitrobenzylidene)toluene-p-sulphonamide (102 mg, 0.33 mmol; J. C. S. Perkin I (1981) 2435-2442) in dichloromethane (2 ml) was added phenyldiazomethane (prepared as in Example 36; 8.11 ml of a 0.074M solution in t-butylmethylether) over a period of 12 hours. Upon completion of the addition the solvent was removed in vacuo and the residue was chromatographed using silica gel elating with 15:85 ethyl acetate:petrol to give the title compound as a mixture of trans and cis isomers. Trans isomer (48 mg, 37%) δH (CDCl3) 8.10-8.19(2H,m), 7.53-7.64(4H,m), 6.95-7.41(7H,m), 4.27(1H,d,J=6 Hz), 4.16(1H,d,J=6 Hz), 2.36(3H,s)ppm. Cis isomer (9 mg; 7%) δH (CDCl3) 8.23-8.33(2H,m); 7.15-7.60(11H,m), 4.13(1H,d,J=2 Hz) 3.87(1H,d,J=2 Hz) 1.68(3H,s)ppm.

Workup

  1. customprepared as in Example 36
  2. additionUpon completion of the addition the solvent
  3. customwas removed in vacuo
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-3a546c5989554edaae12248e383e4923
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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