1,1'-Carbonyldiimidazole → N-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea

HRID 745193

반응식

HRID 745193 반응식
[C:1]1([S:7]([CH2:10][CH2:11][NH2:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[CH2:25]([N:27]([CH2:34][CH3:35])[CH2:28][CH2:29][NH:30][CH:31]([CH3:33])[CH3:32])[CH3:26]>O1CCCC1>[CH2:34]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][N:30]([CH:31]([CH3:33])[CH3:32])[C:13]([NH:12][CH2:11][CH2:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])=[O:14])[CH3:35]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 35454972-(Benzenesulfonyl)ethan-1-amineHCID 12639037Diethyl((2-((propan-2-yl)amino)ethyl))amine

생성물 1

HCID 20152862N-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 6.96 g (0.0376 mole) of 2-phenylsulfonylethanamine and 6.64 g (0.041 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.16 g (0.039 mole) of N-[2-(diethylamino)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 13 hr. The solvent was removed in vacuo, and the residue was dissolved in a 50/50 mixture of ether and methylene chloride. The solution was extracted with water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (methanol) gave 5.74 g (41.36%) of clear, colorless oil: 1H NMR (CDCl3)δ8.5 (br s, 1, NH) 7.46-8.05 (m, 5, aromatic), 4.45 (m, 1, (CH3)2CH), 3.48 (br s, 4, SO2CH2CH 2), 3.0 (t, 2, (CH2CH2N-Et2) 2.3-2.8 (m, 6, CH2N CH2N(CH2CH3)2), 0.90-1.2 (m, 12, CH3 groups).

후처리

  1. temperaturethe mixture was refluxed for 13 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 50/50 mixture of ether and methylene chloride
  4. extractionThe solution was extracted with water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil
  8. customFlash chromatography on silica gel (methanol) gave 5.74 g (41.36%) of clear, colorless oil

출처 및 근거

ORD 기록
ord-0a0c049c547b4c5a88247500ca4f1e1e
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04597902

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