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Dimethyl Sulfoxide → 2-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal

HRID 1847003
Notes
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Reaction equation

HRID 1847003 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]([O:28][CH2:29][O:30][CH3:31])[CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][C:16]1=[O:27].C(N(CC)CC)C>ClCCl>[CH3:31][O:30][CH2:29][O:28][CH:13]([CH2:14][N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][C:16]1=[O:27])[CH:12]=[O:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 867249321-[3-Hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 867249342-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
4×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (0.032 ml, 0.374 mmol) was dissolved in dichloromethane (2 ml). A solution of dimethyl sulfoxide (0.053 ml, 0.748 mmol) in dichloromethane (0.5 ml) was added to this solution at −78° C. and the mixture was stirred for 30 minutes. While maintaining the temperature at −78° C., a solution of 1-[3-hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one (100 mg, 0.340 mmol) in dichloromethane (3 ml) was further added and the mixture was stirred for 40 minutes. While maintaining the temperature at −78° C., triethylamine (0.261 ml, 1.870 mmol) was added and the mixture was stirred for 30 minutes. The temperature was raised to 0° C., the reaction solution was stirred for 2 hours, then diluted with dichloromethane and washed with water. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to yield 109 mg (quantitative) of the title compound in the form of an orange oily product. The product was used as such for the next step without purification.

Workup

  1. stirringthe mixture was stirred for 40 minutes
  2. temperatureWhile maintaining the temperature at −78° C.
  3. stirringthe mixture was stirred for 30 minutes
  4. temperatureThe temperature was raised to 0° C.
  5. stirringthe reaction solution was stirred for 2 hours
  6. washwashed with water
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-56999e63d5554c5b89b6ba4b68c02fff
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08952010B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes