Dimethyl Sulfoxide → HCID 86615013, compound

HRID 732564Notes

Reaction equation

HRID 732564 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].C(Cl)(=O)C(Cl)=O.CS(C)=O.C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Product 1

HCID 86615013HCID 86615013, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Treat a solution 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (5.79 g, 20.7 mmol) in dichloromethane (50 mL) at −78° C. with oxalyl chloride (1.99 mL, 22.8 mmol), DMSO (3.5 mL, 49.5 mmol), and triethylamine (8.6 mL, 62.1 mmol). Stir at −78° C. for 30 min, warm to room temperature and stir for 1 h. Quench with ice and extract with dichloromethane (100 mL). Wash with saturated aqueous NaHCO3, saturated aqueous sodium chloride, dry (magnesium sulfate) concentrate and purify (silica gel chromatography, eluting with 40:60 to 50:50 ethyl acetate:hexanes) to give the title compound (4.53 g, 78%).

Workup

  1. temperaturewarm to room temperature
  2. stirringstir for 1 h
  3. customQuench with ice
  4. extractionextract with dichloromethane (100 mL)
  5. washWash with saturated aqueous NaHCO3, saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate
  8. custompurify
  9. wash(silica gel chromatography, eluting with 40:60 to 50:50 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-e1969ffecb68470bbc30eea040a102c9
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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