Dichloromethane → HCID 86605518, compound

HRID 2374695Notes

Reaction equation

HRID 2374695 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1)C=C.CNS([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([O:47][CH2:48][CH:49]=[CH2:50])(=[O:46])C.[Cl:51]CCl>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:24]1[C:19]([C:44]([O:47][OH:11])=[O:46])=[CH:20][CH:21]=[CH:22][CH:23]=1.[Cl:51][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.[O:47]1[CH2:48][CH:49]1[CH2:50][C:6]1[CH:5]=[C:4]([CH3:1])[CH:9]=[CH:8][C:7]=1[S:10]([NH2:13])(=[O:11])=[O:12]

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 11584Allyl acetateHCID 11776TriphenylphosphineHCID 78858N-MethylbenzenesulfonamideHCID 21039786HCID 21039786, compound

Product 2

HCID 86605518HCID 86605518, compoundHCID 86605519HCID 86605519, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-methyl-N*-allyl-4-benzenesulfonamide was also prepared by stirring N-methyl-4-benzenesulfonamide (4.65 g, 0.025 mol), triphenylphosphine (0.1 g), allyl acetate (10 ml) and palladium acetate (50 mg) for 48 hrs. The reaction mixture was diluted with ethyl acetate and the organic solution washed with water (2×), dilute sodium bicarbonate and dried over anhydrous magnesium sulfate. Evaporation in vacuo gave material that was 95% product and <5% starting material. The oxidation of N-methyl-N*allyl-4-methlbenzenesulfonamide with m-chlorobenzene perbenzoic acid in dichloromethane solution overnight gave N-methyl-N*-(2,3-epoxypropyl)-4-methylbenzenesulfonamide. The IR and NMR spectra were identical to product prepared by method A. A similar experiment with peracetic acid at room temperature required longer reaction times (˜4-5 days).

Workup

  1. washthe organic solution washed with water (2×), dilute sodium bicarbonate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation in vacuo
  4. customgave material that

Sources & evidence

ORD record
ord-eda7bec2f4594b0d9fc0c4b6f26eca60
Source dataset
uspto-grants-2008_12
Patent number
US07462728B2

Reaction notes

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