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

HRID 745198

反応式

HRID 745198 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-baa947ed9950409185797aa317f969a1
出典データセット
uspto-grants-1986_07
特許番号
US04597902

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