Dimethyl Sulfoxide → HCID 11731420, compound

HRID 555320Notes

Reaction equation

HRID 555320 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH:25]([OH:42])[CH2:26][N:27]2[C:39]3[CH:38]=[CH:37][C:36]([Br:40])=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[C:31]([Br:41])[CH:32]=3)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CCOCC.CO>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][N:21]([CH2:24][C:25](=[O:42])[CH2:26][N:27]2[C:39]3[CH:38]=[CH:37][C:36]([Br:40])=[CH:35][C:34]=3[C:33]3[C:28]2=[CH:29][CH:30]=[C:31]([Br:41])[CH:32]=3)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 9915979HCID 9915979, compoundHCID 21864698Diethyl ether methanol

Product 1

HCID 11731420HCID 11731420, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

At −78° C. a solution of oxalyl chloride (200 μL, 2.34 mmol) in anhydrous DCM (20 mL) is treated with anhydrous DMSO (310 μL, 4.37 mmol). After 15 min of stirring at −78° C., a solution of Example 4 (1.0 g, 1.76 mmol) in anhydrous DCM (5 mL) is added dropwise. The resulting mixture is allowed to stir for 40 min at −78° C. and TEA (1250 μL) is added neat. After 10 min the reaction mixture is allowed to warm up to −30° C. After 1 hour of stirring at −30° C. the reaction mixture is quenched with water (50 mL). Extraction with DCM (3×100 mL), drying over MgSO4 and evaporation under reduced pressure gives a yellow oil. Flash chromatography on a 4×21 cm2 SiO2 column using Et2O/MeOH (100/1) mixture then (100/3) as eluant gives the title compound as a pale yellow foam (0.804 g, 1.42 mmol) in a 81% yield.

Workup

  1. stirringto stir for 40 min at −78° C.
  2. waitAfter 10 min the reaction mixture is allowed
  3. temperatureto warm up to −30° C
  4. stirringAfter 1 hour of stirring at −30° C. the reaction mixture
  5. customis quenched with water (50 mL)
  6. extractionExtraction with DCM (3×100 mL)
  7. dry with materialdrying over MgSO4 and evaporation under reduced pressure
  8. customgives a yellow oil

Sources & evidence

ORD record
ord-a5f3880e843847bdaae86f36749f8dfa
Source dataset
uspto-grants-2011_11
Patent number
US08053436B1

Reaction notes

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