Hydrochloric Acid → HCID 19873523, compound

HRID 465277Notes

Reaction equation

HRID 465277 reaction equation
[H-].[Na+].[CH3:3][NH:4][S:5]([N:8]([CH3:11])[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>[CH3:11][N:8]([O:9][CH3:10])[S:5]([N:4]([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])[CH3:3])(=[O:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 19873524HCID 19873524, compoundHCID 22058798Phenyl (chlorosulfonyl)carbamate

Product 1

HCID 19873523HCID 19873523, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

1.15 g (28.8 mmol) of 60% sodium hydride was washed with n-hexane, and dry THF was added, and the mixture was cooled with ice. To this mixture, a THF solution containing 2 g (13 mmol) of N,N'-dimethyl-N'-methoxysulfamide was dropwise added. After stirring the mixture for 10 minutes, a dry THF solution containing 3.21 g (13.6 mmol) of phenyl N-chlorosulfonylcarbamate was dropwise added thereto. The mixture was stirred at room temperature for 7 hours. The reaction mixture was poured into 500 ml of ice water containing 3.5 g of 35% hydrochloric acid and extracted three times with diethyl ether. The diethyl ether layer was washed sequentially with water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 4.3 g of phenyl N-[(N-(N-methyl N-methoxyaminosulfonyl)-N-methylamino)sulfonyl]carbamate as slightly yellow oil.

Workup

  1. additionwas added
  2. temperaturethe mixture was cooled with ice
  3. additionwas dropwise added
  4. additionwas dropwise added
  5. stirringThe mixture was stirred at room temperature for 7 hours
  6. extractionextracted three times with diethyl ether
  7. washThe diethyl ether layer was washed sequentially with water
  8. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cd1fc3bf358a4e3fb60fdf847c804537
Source dataset
uspto-grants-1992_10
Patent number
US05152824

Reaction notes

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