Sulfamide → HCID 18538719, compound

HRID 412938Notes

Reaction equation

HRID 412938 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:34](N)([NH2:37])(=[O:36])=[O:35]>CC(O)C>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:18]([CH:20]2[CH2:21][CH2:22][N:23]([S:34](=[O:36])(=[O:35])[NH2:37])[CH2:24][CH2:25]2)=[O:19])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 18538605HCID 18538605, compound

Product 1

HCID 18538719HCID 18538719, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of the compound obtained in Example 66 (391 mg, 0.80 mmol), sulfamide (1.54 g, 16.0 mmol), 2-propanol (20 mL) and distilled water (10 mL) was stirred under reflux for 4 days. The reaction mixture was concentrated under reduced pressure, and to the concentrate was added a saturated aqueous solution of sodium hydrogen carbonate. The mixture was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (silica gel 10 g, ethyl acetate/methanol=1/0 to 9/1), and the desired fraction was concentrated under reduced pressure. To the concentrate were added diethyl ether and ethyl acetate, and the resulting precipitates were collected by filtration. The precipitates were washed with diethyl ether, and dried under reduced pressure to give the titled compound (230 mg, 0.41 mmol, Yield 51%) as white crystals.

Workup

  1. distillationdistilled water (10 mL)
  2. temperatureunder reflux for 4 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the concentrate was added a saturated aqueous solution of sodium hydrogen carbonate
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationthe desired fraction was concentrated under reduced pressure
  9. additionTo the concentrate were added diethyl ether and ethyl acetate
  10. customthe resulting precipitates
  11. filtrationwere collected by filtration
  12. washThe precipitates were washed with diethyl ether
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-57853557b3f74f3095a6524f6887a03f
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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