Dimethyl Sulfoxide → HCID 86743024, compound

HRID 1761972Notes

Reaction equation

HRID 1761972 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19](CO)=[C:20]([CH:29]([CH3:31])[CH3:30])[S:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:19][C:20]([CH:29]([CH3:31])[CH3:30])([CH:2]=[O:3])[S:21][C:22]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10663905HCID 10663905, compound

Product 1

HCID 86743024HCID 86743024, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.92 g of oxalyl chloride in 50 ml of methylene chloride at -78° was added dropwise a solution of 2.22 g of dimethylsulfoxide in 25 ml methylene chloride. After stirring at -78° for 10 minutes, a solution of 4.0 g of the title methanol product of Step 1, above, in 30 ml of methylene chloride was added dropwise. The mixture was stirred at -78° for 1 hour. Then 2.5 g of triethylamine was added. The mixture was allowed to warm to R.T., then was poured into water. The organic phase was separated and the solvent was removed under reduced pressure. The residue was dissolved in MTBE and washed with water. The organic solution was dried, and the solvent was removed under reduced pressure to give 3.8 g or the title product of this step. A sample of which was triturated with pentane to give refined product. M.P. 116°-120°.

Workup

  1. stirringThe mixture was stirred at -78° for 1 hour
  2. customThe organic phase was separated
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in MTBE
  5. washwashed with water
  6. customThe organic solution was dried
  7. customthe solvent was removed under reduced pressure
  8. customto give 3.8 g

Sources & evidence

ORD record
ord-0a1edec349a94a4699b29bd40ebe3968
Source dataset
uspto-grants-1989_05
Patent number
US04829081

Reaction notes

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