Hydrochloric Acid → HCID 19873532, compound

HRID 465275Notes

Reaction equation

HRID 465275 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:11])[S:5]([NH:8][O:9][CH3:10])(=[O:7])=[O:6].Cl[S:13]([NH:16][C:17](=[O:25])[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:15])=[O:14].Cl>CCCCCC.C1COCC1>[CH3:3][N:4]([CH3:11])[S:5]([N:8]([S:13]([NH:16][C:17](=[O:25])[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:14])=[O:15])[O:9][CH3:10])(=[O:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 19873533HCID 19873533, compoundHCID 22058798Phenyl (chlorosulfonyl)carbamate

Product 1

HCID 19873532HCID 19873532, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

2.69 g (61.5 mmol) of 55% sodium hydride was washed with n-hexane and then suspended in 100 ml of dry THF. Then, 4.62 g (30 mmol) of N,N-dimethyl-N'-methoxysulfamide dissolved in 20 ml of THF was dropwise added thereto under cooling with ice. The mixture is heated to room temperature and then stirred at room temperature for one hour. Then, this reaction mixture was again cooled with ice, and 7.07 g (30 mmol) of phenyl N-chlorosulfonylcarbamate dissolved in 30 ml of dry THF was dropwise added thereto. The mixture was heated to room temperature and then stirred at room temperature for 30 minutes. The reaction mixture was poured into 500 ml of ice water containing 6.4 g of 35% hydrochloric acid and extracted three times with 80 ml of diethyl ether. The extract solution was washed three times with 100 ml of water and once with 100 ml of a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 10.1 g of phenyl N-[(N-dimethylsulfamoyl-N-methoxyamino)sulfonyl]carbamate as slightly yellow oil.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice
  3. additionwas dropwise added
  4. temperatureThe mixture was heated to room temperature
  5. stirringstirred at room temperature for 30 minutes
  6. extractionextracted three times with 80 ml of diethyl ether
  7. washThe extract solution was washed three times with 100 ml of water
  8. dry with materialonce with 100 ml of a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7cde9cd9113e471496d99f206fa743cc
Source dataset
uspto-grants-1992_10
Patent number
US05152824

Reaction notes

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