Dimethyl Sulfoxide → HCID 21472503, compound

HRID 2294994Notes

Reaction equation

HRID 2294994 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:34][CH2:35][OH:36])[CH2:20][C:21]([N:23]([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].CCN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:34][CH:35]=[O:36])[CH2:20][C:21]([N:23]([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19029344HCID 19029344, compound

Product 1

HCID 21472503HCID 21472503, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cool a solution of oxalyl chloride (1.43 mL) in CH2Cl2 (30 mL) to -78° C., add DMSO (2.32 mL) dropwise over 15 mins., stir for 15 min., then add a CH2Cl2 (20 mL) solution of the product of Step 5 (1.3 g) over 20 min. Stir the mixture for 30 min, treat with Et3N (9.2 mL) and stir for an additional 30 min. at -78° C., followed by 1.5 h at room temperature. Quench the reaction mixture with water and dilute with CH2Cl2 (100 mL). Separate the organic fraction, wash sequentially with 1N HCl (1×50 mL), sat. NaHCO3 (1×50 mL) and brine (1×50 mL), dry over MgSO4, filter and concentrate under reduced pressure to yield an oil. Chromatograph on silica gel, eluting with 50-100% EtOAc/hexane to give 3,4-dichloro-β-(2-oxoethyl)-N-methyl-N-[(2-methoxyphenyl)methyl] benzenepropanamide (950 mg).

Workup

  1. stirringStir the mixture for 30 min
  2. stirringstir for an additional 30 min. at -78° C.
  3. waitfollowed by 1.5 h at room temperature
  4. customQuench the reaction mixture with water
  5. additiondilute with CH2Cl2 (100 mL)
  6. customSeparate the organic fraction
  7. washwash sequentially with 1N HCl (1×50 mL), sat. NaHCO3 (1×50 mL) and brine (1×50 mL)
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. customto yield an oil
  12. washChromatograph on silica gel, eluting with 50-100% EtOAc/hexane

Sources & evidence

ORD record
ord-75390ab45cfb4759b89b47e55f4ded01
Source dataset
uspto-grants-1997_11
Patent number
US05691362

Reaction notes

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