Dimethyl Sulfoxide → HCID 18419520, compound

HRID 989894Notes

Reaction equation

HRID 989894 reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.OC(C)[CH2:13][CH2:14][N:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N+:24]=1[O-])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CCN(CC)CC>C(Cl)Cl>[C:19]([O:18][C:16]([N:15]([CH2:14][CH2:13][CH2:6][CH:5]=[O:9])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18419521HCID 18419521, compound

Product 1

HCID 18419520HCID 18419520, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of DMSO (0.31 mL, 3.54 mmole) in CH2Cl2 (5 mL) at −78° C. was added oxalyl chloride (0.13 mL, 1.77 mmole) dropwise. After 10 min, a solution of 2-[N-(3-hydroxy-1-butyl)-N-(tert-butoxycarbonyl)amino]pyridine-N-oxide (500 mg, 1.77 mmole) in CH2Cl2 (5 mL) was added dropwise. After 30 min, Et3N (0.81 mL, 5.84 mmole) was added, and the mixture was warmed gradually to RT. After 20 min, the mixture was diluted with CH2Cl2 (20 mL) and washed sequentially with 10 mL each H2O, 10% HCl, H2O, and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (455 mg, 92%) as a colorless oil. This was used without purification: MS. (ES) m/e 281 (M+H)+.

Workup

  1. waitAfter 30 min
  2. waitAfter 20 min
  3. washwashed sequentially with 10 mL each H2O, 10% HCl, H2O, and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-327e218c85b84477a9a981b7a14d6b16
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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