Dimethyl Sulfoxide → HCID 87279390, compound

HRID 2167957Notes

Reaction equation

HRID 2167957 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[O:21][CH2:20][C:19]=2[CH2:26][OH:27])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.CCOCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][C:22]([CH3:24])([CH3:25])[O:21][CH2:20][C:19]=2[CH:26]=[O:27])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67126442HCID 67126442, compound

Product 1

HCID 87279390HCID 87279390, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (1.1 g) in dichloromethane (30 mL) at −78° C. was added dimethylsulfoxide (6.12 mL). The mixture was stirred at the temperature for 30 minutes, and then a solution of EXAMPLE 15D (1.2 g) in dichloromethane (10 mL) was added. The mixture was stirred at −78° C. for 2 hours before the addition of triethylamine (10 mL). The mixture was stirred overnight and the temperature was allowed to rise to room temperature. The mixture was diluted with ether (300 mL) and washed with water, brine and dried over Na2SO4. Concentration of the solvent and column purification (5% ethyl acetate in hexane) gave the product.

Workup

  1. stirringThe mixture was stirred overnight
  2. customto rise to room temperature
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. customConcentration of the solvent and column purification (5% ethyl acetate in hexane)
  6. customgave the product

Sources & evidence

ORD record
ord-f96ff9f0cd344b00b045e6878b18ddb7
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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