2-(Chloromethyl)aniline hydrochloride → HCID 15027412, Verbindung

HRID 1646698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646698
[SH:1][C:2]1[NH:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[N:3]=1.Cl.[NH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl>C(O)C>[NH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][S:1][C:2]1[NH:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[N:3]=1

Komponenten

4

Edukt 2

HCID 123879412-(Chloromethyl)aniline hydrochlorideHCID 1785278154,5,6,7-tetrahydro-1H-benzimidazole-2-thiol

Produkt 1

HCID 15027412HCID 15027412, VerbindungAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 1.5 g (purity 75%, 7.3 mmol) of 2-mercapto-4,5,6,7-tetrahydro-1H-benzimidazole in 15 ml of ethanol was added 1.3 g (7.3 mmol) of 2-aminobenzyl chloride hydrochloride, and the mixture was stirred for 2 hrs. at room temperature. Ethanol was distilled off under reduced pressure at room temperature. The residue was made alkaline by addition of saturated aqueous sodium hydrogencarbonate and then extracted with 40 ml of chloroform. The chloroform portion was washed with 10 ml of 0.2N NaOH and then with saturated aqueous sodium chloride. The washed chloroform portion was dried over anhydrous sodium sulfate and placed under reduced pressure to distill off the solvent. The residue was purified by silica gel column chromatography using chloroform-methanol to give 1.35 g of the desired compound as a pale yellow oil, yield 71.4%.

Aufarbeitung

  1. customat room temperature
  2. distillationEthanol was distilled off under reduced pressure at room temperature
  3. additionby addition of saturated aqueous sodium hydrogencarbonate
  4. extractionextracted with 40 ml of chloroform
  5. washThe chloroform portion was washed with 10 ml of 0.2N NaOH
  6. dry with materialThe washed chloroform portion was dried over anhydrous sodium sulfate
  7. distillationto distill off the solvent
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7d95fe21a8454b3185a13827bafa3bbc
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05180836

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