Diethylamine → HCID 19777925, compound

HRID 1195131Notes

Reaction equation

HRID 1195131 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9]([CH2:12][N+:13]([O-:15])=[O:14])(=[O:11])=[O:10])=[C:4]([CH3:16])[CH:3]=1.[C:17](Cl)(=[O:21])[C:18](Cl)=[O:19].C(=O)([O-])[O-].[Ca+2].[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29]>C(COC)OC>[CH2:28]([N:30]([CH2:31][CH3:32])[C:18]([C:17]([NH:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([S:9]([CH2:12][N+:13]([O-:15])=[O:14])(=[O:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1)=[O:21])=[O:19])[CH3:29]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 10112Calcium CarbonateHCID 65578Oxalyl chlorideHCID 195716Ici 222155

Product 1

HCID 19777925HCID 19777925, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(4-Amino-2,6-dimethylphenylsulfonyl)nitromethane (1.0 g) was added in portions during 10 minutes to a stirred solution of oxalyl chloride (2.0 g) in dimethoxyethane (50 mL) containing calcium carbonate (1.63 g), maintained at about 0°-5° C. The mixture was then further stirred at the same temperature for 30 minutes. Diethylamine (3.4 g) was then added dropwise during 5 minutes. When the addition was complete, the reaction mixture was allowed to attain ambient temperature and the solvent was removed by evaporation in vacuo. Water (50 mL) was then added. The solid which formed was collected by filtration and purified by chromatogaphy on silica using toluene containing increasing amounts of ethyl acetate as eluant. The solid obtained from the major fractions was crystallised first from carbon tetrachloride and then from 2-propanol to give N,N-diethyl-N'-(3,5-dimethyl-4-[nitromethylsulfonyl]phenyl)oxamide as a solid, m.p. 128°-129° C.; microanalysis, found: C,48.2; H,5.5; N,11.2%; C15H21N3O6S requires: C,48.5; H,5.7; N,11.3%.

Workup

  1. temperaturemaintained at about 0°-5° C
  2. additionWhen the addition
  3. customto attain ambient temperature
  4. customthe solvent was removed by evaporation in vacuo
  5. additionWater (50 mL) was then added
  6. customThe solid which formed
  7. filtrationwas collected by filtration
  8. custompurified by chromatogaphy on silica
  9. temperatureincreasing amounts of ethyl acetate as eluant
  10. customThe solid obtained from the major fractions
  11. customwas crystallised first from carbon tetrachloride

Sources & evidence

ORD record
ord-ef8acba412134aadb524108fda0b3905
Source dataset
uspto-grants-1992_05
Patent number
US05110808

Reaction notes

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