Dimethyl Sulfoxide → HCID 131725264, compound

HRID 1611716Notes

Reaction equation

HRID 1611716 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=[CH:13][C:14]=1[CH2:15][OH:16].C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[C:15]=[O:16])[CH:13]=[CH:12][C:11]([NH:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:10]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22254172HCID 22254172, compound

Product 1

HCID 131725264HCID 131725264, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Using the method of Swern, et al., N-(2-{[3-(2,4-dichlorophenyl)-4-(hydroxymethyl)phenyl]amino}ethyl)(tert-butoxy)carboxamide (100 mg) is dissolved in anhydrous methylene chloride (1 ml) and added to a premixed solution of oxalyl chloride (1.5 eq) and DMSO (3 eq) in methylene chloride (25 ml) which has been stirring at −78° C. for 15 min. The resulting solution is stirred at −78° C. for an additional 30 min, at which time triethyl amine (6 eq) is added. The resulting suspension is allowed to warm to room temperature. After 15 min., water (1 ml) is added and the layers separated. The aqueous layer is extracted with methylene chloride (2×10 ml), and the combined organic layers dried (sodium sulfate) and concentrated to afford aldehyde 8 in 70–80% yield as a light yellow foam. This product proves to be unstable and is used without further manipulation.

Workup

  1. additionis added
  2. temperatureto warm to room temperature
  3. waitAfter 15 min.
  4. customthe layers separated
  5. extractionThe aqueous layer is extracted with methylene chloride (2×10 ml)
  6. dry with materialthe combined organic layers dried (sodium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0fb36b2eb0b44c73b6a1af7dae86f6d7
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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