Dimethyl Sulfoxide → HCID 21904386, compound

HRID 1839229Notes

Reaction equation

HRID 1839229 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:24][CH2:23][CH:22]2[C:20]([CH2:25][OH:26])([CH2:21]2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO.CCN(CC)CC>[CH2:11]([N:18]1[CH2:24][CH2:23][CH:22]2[C:20]([CH:25]=[O:26])([CH2:21]2)[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 21904380HCID 21904380, compound

Product 1

HCID 21904386HCID 21904386, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Procedure

To a solution of oxalyl chloride (0.22 ml, 2.54 mmol) in CH2Cl2 (2 ml) at −55° C. was added a solution of DMSO (0.30 ml, 4.24 mmol) in CH2Cl2 (1 ml). The mixture was stirred for 2 min. Then, a solution of 173 (230 mg, 1.06 mmol) in CH2Cl2 (1 ml) was added dropwise. After stirring for 15 min at −55° C., Et3N (1.4 ml) was added slowly. The mixture was stirred for 5 min and then warmed to room temperature. Aqueous NaHCO3 (5 ml) was added. The two layers were separated; and the aqueous layer was extracted with CH2Cl2 (2×5 ml). The combined organics were dried (Na2SO4), filtered and evaporated to give the crude product. Chromatography (1% MeOH in CH2Cl2) gave 174 as a light red liquid. 1H-NMR (300 MHz, CDCl3) (partial) δ 9.42 (s, 1H), 7.30 (m, 5H); LRMS (calculated for C14H17NO) 215, found 215.

Workup

  1. stirringAfter stirring for 15 min at −55° C.
  2. stirringThe mixture was stirred for 5 min
  3. customThe two layers were separated
  4. extractionand the aqueous layer was extracted with CH2Cl2 (2×5 ml)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give the crude product

Sources & evidence

ORD record
ord-3a91f3d04f914768991c8bb82528b386
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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