N,N-Diethylethylenediamine → N'-[2-(Dimethylamino)ethyl]-N-(1-methylethyl)-N-[4-(phenylsulfonyl)butyl]urea hydrate

HRID 745197노트

반응식

HRID 745197 반응식
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19]C)[CH2:16][CH2:17][NH2:18])C.[CH3:21][CH:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH3:23]>O1CCCC1.C(Cl)(Cl)Cl>[OH2:2].[CH3:19][N:15]([CH3:13])[CH2:16][CH2:17][NH:18][C:1](=[O:2])[N:24]([CH:22]([CH3:21])[CH3:23])[CH2:25][CH2:26][CH2:27][CH2:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:30])=[O:31]

참가 물질

6

반응물 3

HCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655072N-(1-methylethyl)-4-(phenylsulfonyl]-1-butylamine

생성물 1

HCID 86740886N'-[2-(Dimethylamino)ethyl]-N-(1-methylethyl)-N-[4-(phenylsulfonyl)butyl]urea hydrate수율 74.9%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1,1'-carbonyldiimidazole (6.00 g, 0.037 mole) and N,N-diethylethylenediamine (4.00 g, 0.034 mole) was stirred at room temperature for 2 hours in 200 ml of tetrahydrofuran. A solution of N-(1-methylethyl)-4-[phenylsulfonyl]-1-butylamine (free base 7.99 g, 0.0313 mole) in 100 ml of tetrahydrofuran was added and the solution was heated overnight at reflux. The reaction was stripped to dryness and the residue dissolved in chloroform. The chloroform was extracted with water, dried (sodium sulfate), filtered, and removed in vacuo. A dark brown oil was obtained upon removal of chloroform. This oil was subjected to flash chromatography on Silica Gel using 0.1N ammonium hydroxide-methanol for elution. This chromatography furnished 5.37 g (42.2% yield) of clear oil after drying in vacuo 18 hours at 60° C. 1H NMR (CDCl3)δ7.8 (m, 5, aromatic), 5.25 (t, 1, NH), 4.15 (m, 1, methine), 3.2 (m, 6, SO2CH2 and methylenes adjacent to amide nitrogen, 2.5), (m, 6, ##STR28## 1.7 (m, 4, aliphatic--CH2CH2), 1.1 (m, 12, CH3).

후처리

  1. temperaturethe solution was heated overnight
  2. temperatureat reflux
  3. extractionThe chloroform was extracted with water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customremoved in vacuo
  7. customA dark brown oil was obtained upon removal of chloroform
  8. washThis oil was subjected to flash chromatography on Silica Gel using 0.1N ammonium hydroxide-methanol for elution

출처 및 근거

ORD 기록
ord-894cde5f748548c09385d7af9b17257c
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04597902

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