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Carbon Disulfide → HCID 178491102、化合物

HRID 249018
ノート
印刷プレビュー

反応式

HRID 249018 の反応式
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:43]([C:47]1[S:48][CH:49]=[C:50]([CH2:52][S:53][CH2:54][CH2:55][NH2:56])[N:51]=1)[C:44]([NH2:46])=[NH:45].[C:57](=S)=[S:58]>CCOCC.C(O)C>[NH:43]([C:47]1[S:48][CH:49]=[C:50]([CH2:52][S:53][CH2:54][CH2:55][NH:56][C:57]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]2[CH:26]=[CH:27][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH3:25])=[S:58])[N:51]=1)[C:44]([NH2:46])=[NH:45]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6348Carbon DisulfideHCID 10868DicyclohexylcarbodiimideHCID 19762600N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamineHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

生成物 1

HCID 178491102HCID 178491102、化合物

試薬・触媒・溶媒 2

HCID 702
Ethanol
溶媒
HCID 3283Diethyl Ether溶媒

実験手順

0.48 g (1.3 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine and 0.27 g (1.3 mmol) of dicyclohexylcarbodiimide are dissolved at -10° C. in absolute ether with 0.5 ml of carbon disulfide, the temperature is increased in the course of 3 hours to 20° C. and the batch is stirred for a further 12 hours. The solid that precipitates is filtered off and the filtrate is concentrated in vacuo. 0.30 g (1.3 mmol) of 2-[[(2-guanidino-4-thiazolyl)methyl]thio]ethaneamine dissolved in a small amount of absolute ethanol is added to the concentrated residue and the reaction batch is heated under reflux for 2 hours. It is then concentrated in vacuo and the residue is purified by rotation chromatography to yield the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=644 ([M+H]+, 1), 121 (100). For further analysis, a portion of the compound is converted into the tartaric acid salt and recrystallised from acetonitrile/isopropanol/petroleum ether; m.p.: 78° C. (acetonitrile/isopropanol/petroleum ether).

後処理

  1. temperaturethe temperature is increased in the course of 3 hours to 20° C.
  2. customThe solid that precipitates
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. additionis added to the concentrated residue
  6. temperaturethe reaction batch is heated
  7. temperatureunder reflux for 2 hours
  8. concentrationIt is then concentrated in vacuo
  9. customthe residue is purified by rotation chromatography
  10. customto yield the
  11. custompurified title compound in the form of a viscous oil
  12. customrecrystallised from acetonitrile/isopropanol/petroleum ether

出典と根拠

ORDレコード
ord-655f31a5490d4c1084f13bc62ce511be
出典データセット
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05212187

反応ノート

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