Dimethyl Sulfoxide → HCID 14882986, compound

HRID 868384Notes

Reaction equation

HRID 868384 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:14]1[CH:39]=[CH:38][C:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:34]=[CH:33][C:26]3[CH2:27][CH2:28][CH:29]([CH2:31][OH:32])[O:30][C:25]=3[C:24]=2[CH2:35][CH2:36][CH3:37])=[C:16]([CH2:40][CH2:41][CH3:42])[C:15]=1[O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=[O:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[C:11]([C:14]1[CH:39]=[CH:38][C:17]([O:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:34]=[CH:33][C:26]3[CH2:27][CH2:28][CH:29]([CH:31]=[O:32])[O:30][C:25]=3[C:24]=2[CH2:35][CH2:36][CH3:37])=[C:16]([CH2:40][CH2:41][CH3:42])[C:15]=1[O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13920775HCID 13920775, compound

Product 1

HCID 14882986HCID 14882986, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.2 ml (13.3 mmole) of oxalyl chloride in 30 ml of methylene chloride was cooled to -70°, and a solution of 1.9 ml (26.6 mmole) of dimethylsulfoxide in 9 ml of methylene chloride was added. The mixture was stirred for 5 minutes and a solution of 6.6 g (12.1 mmole) of the title compound of Example 39 in 20 ml of methylene chloride was added. After stirring an additional 15 minutes, 8.5 ml (60.5 mmole) of triethylamine was added, and the mixture was stirred at -70° for 5 minutes and allowed to warm to room temperature. Water was added and the layers were separated. The organic layer was washed successively with dilute hydrochloric acid, 5% sodium bicarbonate solution, water and brine, dried over MgSO4, and filtered. Removal of the solvent gave 6.44 g of the title compound as a yellow oil. Structure assignment was supported by nmr and infrared spectra.

Workup

  1. stirringAfter stirring an additional 15 minutes
  2. stirringthe mixture was stirred at -70° for 5 minutes
  3. customthe layers were separated
  4. washThe organic layer was washed successively with dilute hydrochloric acid, 5% sodium bicarbonate solution, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-fb445c8624e44cd2bcbb8e85826f96d2
Source dataset
uspto-grants-1988_10
Patent number
US04778903

Reaction notes

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