1,2-Dimethoxyethane → HCID 20690187, compound

HRID 903018Notes

Reaction equation

HRID 903018 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[CH2:19]([N:21](CC)CC)[CH3:20].COCC[O:30][CH3:31]>>[CH3:31][O:30][CH2:20][CH2:19][N:21]([S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[C:2]([C:1]([N:11]([CH2:10][CH2:9][O:8][CH3:7])[S:12]([C:15]([F:18])([F:16])[F:17])(=[O:13])=[O:14])=[O:5])=[O:3]

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 205712571,1,1-Trifluoro-N-(2-methoxyethyl)methanesulfonamide

Product 1

HCID 20690187HCID 20690187, compound

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (1.27 grams; 0.01 mole) is added portionwise to a stirred solution of N-(2-methoxyethyl)trifluoromethanesulfonamide (4.0 grams; 0.02 mole) and triethylamine (2.0 grams; 0.02 mole) in 1,2-dimethoxyethane (40 mls) at 0° C. under a nitrogen atmosphere. After the addition is completed, the reaction mixture is stirred at 0° C. for one hour, heated to 50° C. and stirred thereat for 2 hours, and concentrated to remove the solvent. The residue is then extracted with diethyl ether and the ether extract is evaporated to obtain 4.65 grams (99% of theoretical) of crude product.

Workup

  1. additionAfter the addition
  2. temperatureheated to 50° C.
  3. stirringstirred
  4. waitfor 2 hours
  5. concentrationconcentrated
  6. customto remove the solvent
  7. extractionThe residue is then extracted with diethyl ether
  8. extractionthe ether extract
  9. customis evaporated
  10. customto obtain 4.65 grams (99% of theoretical) of crude product

Sources & evidence

ORD record
ord-8d48518e5e9446b5b81fa8a5a81df680
Source dataset
uspto-grants-1980_10
Patent number
US04226738

Reaction notes

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