Triethylamine → Sulfamic acid 4-oxo-4-phenylbutyl ester

HRID 1613392Notes

Reaction equation

HRID 1613392 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].[O:8]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][CH2:11][CH2:12][OH:13].C(N(CC)CC)C.S(Cl)(=O)(=O)N>C(Cl)Cl.C(#N)C.O>[O:8]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:10][CH2:11][CH2:12][O:13][S:2](=[O:3])(=[O:4])[NH2:5]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 70918Chlorosulfonyl isocyanateHCID 109758164-Hydroxy-1-phenylbutan-1-one

Product 1

HCID 54177453Sulfamic acid 4-oxo-4-phenylbutyl esterYield 40.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A cold (-10° C.) solution of 5.20 ml (0.06 mole) chlorosulfonyl isocyanate in 50 ml of methylene chloride was treated with a solution of 0.11 ml of water in 5 ml of acetonitrile over a period of 30 min. A solution of 6.56 g (0.04 mole) of 4-oxo-4-phenylbutanol and 8.34 ml (0.06 mole) of triethylamine in 30 ml of methylene chloride was then added to the solution of the sulfamoyl chloride at 0° to 10° C. over 20 min. The reaction mixture was stirred at room temperature for 4 hr. extracted once with water and once with sodium bicarbonate solution. The aqueous layers were back extracted with methylene chloride. The combined organic layers were dried (magnesium sulfate) and concentrated to an oil that solidified on standing. The solid was triturated with 1,1,1-trichloroethane to give 3.90 g of off-white solid. Recrystallization from acetonitrile-1,1,1-trichloroethane yielded 3.2 g of off-white solid, mp 78°-80° C.

Workup

  1. extractionextracted once with water and once with sodium bicarbonate solution
  2. extractionThe aqueous layers were back extracted with methylene chloride
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. concentrationconcentrated to an oil that
  5. customThe solid was triturated with 1,1,1-trichloroethane

Sources & evidence

ORD record
ord-c570350945e148aa977fe4eb8ad6969d
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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