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

HRID 327687ノート

反応式

HRID 327687 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 54177453Sulfamic acid 4-oxo-4-phenylbutyl ester収率 40.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b645d68d8b9b487d931f8b626348d6b1
出典データセット
uspto-grants-1993_12
特許番号
US05273993

反応ノート

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