Dimethyl Sulfoxide → HCID 53838613, compound

HRID 2231154Notes

Reaction equation

HRID 2231154 reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([OH:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].C([O-])([O-])=O.[K+].[K+].CS(C)=O.[CH2:32](I)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>Cl.CCOCC.CCCCCC.O.C(Cl)Cl>[CH3:21][N:2]([CH3:1])[C:3](=[O:20])[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([O:14][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13]

Participants

9

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 12098Benzyl iodideHCID 67899397HCID 67899397, compound

Product 1

HCID 53838613HCID 53838613, compoundYield 31.8%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
120 °C

Procedure

A well stirred slurry of 10.0 g of N,N-dimethylalphaethoxycarbonyl-beta-hydroxy-2,4-dichlorocinnamamide, 8.3 g of powdered anh. K2CO3, and 100 ml of dry DMSO was heated to 100° C. for 30 min. To this mixture was added 6.5 g of benzyl iodide all at once and the mixture heated at 120° C. for 1 hour. The reaction was cooled to RT, 100 ml of CH2Cl2 and 100 ml of water added plus a few drops of concentrated HCl. The organic phase was collected, washed with saturated brine, dried with MgSO4, filtered and concentrated under reduced pressure to yield a light yellow gum. The crude product was taken up in a minimum amount of ether/hexane and the product allowed to crystallize, yielding 4.0 g of white solid, MP 115° C.

Workup

  1. temperatureThe reaction was cooled to RT
  2. customThe organic phase was collected
  3. washwashed with saturated brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a light yellow gum
  8. customto crystallize

Sources & evidence

ORD record
ord-d8ac1c0dd77247acad22889821b6fa38
Source dataset
uspto-grants-1988_11
Patent number
US04781750

Reaction notes

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