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

HRID 327687노트

반응식

HRID 327687 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

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-trichlorethane yielded 3.2 g of off-white solid, mp 78°-80° C.

후처리

  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

출처 및 근거

ORD 기록
ord-b645d68d8b9b487d931f8b626348d6b1
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273993

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