Methanol → N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[5-(phenylsulfonyl)pentyl]urea hydrate

HRID 745198

반응식

HRID 745198 반응식
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH2:18])[CH3:14].[CH3:21][CH:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])[CH3:23].[CH3:39][OH:40]>O1CCCC1.C(Cl)(Cl)Cl>[OH2:2].[CH2:13]([N:15]([CH2:19][CH3:20])[CH2:16][CH2:17][NH:18][C:39](=[O:40])[N:24]([CH:22]([CH3:23])[CH3:21])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)(=[O:32])=[O:31])[CH3:14]

참가 물질

7

반응물 4

HCID 887MethanolHCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655070N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine

생성물 1

HCID 20152837N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[5-(phenylsulfonyl)pentyl]urea hydrate수율 66.6%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1,1'-carbonyldiimidazole (4.54 g, 0.028 mole) and N,N-diethylethylenediamine (2.90 g, 0.025 mole) in tetrahydrofuran was stirred for 1 hr at room temperature. A solution of N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine (6.74 g, 0.025 mole) in tetrahydrofuran (dried over 4 A molecular sieves) was added and the resulting solution was heated over night at gentle reflux. The reaction mixture was stripped to dryness and the residue dissolved in chloroform. The chloroform layer was extracted with water, dried (anhydrous sodium sulfate), filtered and the solvent removed to give a brown oil. The brown oil was subjected to flash column chromatography on Silica Gel using methanol for elution. Fractions of similar purity were combined, solvent removed, and the oil dried in vacuo at 60° C. overnight. This produced 7.00 g (66.6% yield) of brown oil. 1H NMR (CDCl3), δ7.8 (m, 5, aromatic), 5.2 (b, 1, NH), 4.2 (m, 1, methine), 3.2 (m, 6, methylenes next to SO2 and amide), 2.5 (m, 7, 1/2 H2O and methylenes next to amine), 1.6 (m, 6, methylenes between SO2 and amide), 1.1 (m, 12, CH3).

후처리

  1. additionwas added
  2. temperaturethe resulting solution was heated over night at gentle reflux
  3. extractionThe chloroform layer was extracted with water
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto give a brown oil
  8. washfor elution
  9. customsolvent removed
  10. customthe oil dried in vacuo at 60° C. overnight

출처 및 근거

ORD 기록
ord-baa947ed9950409185797aa317f969a1
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04597902

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