N-Ethylbenzylamine → HCID 67710926, compound

HRID 1378311Notes

Reaction equation

HRID 1378311 reaction equation
[Cl:1][C:2]1[C:3]([C:13]2[N:17]([S:18][CH3:19])[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[N:14]=2)=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:10][CH2:11]Cl)[CH3:9].[CH2:24]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:25]>>[ClH:1].[ClH:1].[ClH:1].[Cl:1][C:2]1[C:3]([C:13]2[N:17]([S:18][CH3:19])[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[N:14]=2)=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([CH2:10][CH2:11][N:26]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:24][CH3:25])[CH3:9]

Participants

3

Reactant 2

HCID 84352N-EthylbenzylamineHCID 22911180HCID 22911180, compound

Product 1

HCID 67710926HCID 67710926, compound

Procedure

2-{3-Chloro-4-[N-(2-chloroethyl)-N-methylamino]-2-pyridyl}-methylthio-1H-benzimidazole (500 mg/1.24 mmol) are heated in N-ethylbenzylamine (15 ml) at 140° C. for 4.5 h. Then the excess N-ethylbenzylamine is removed by distillation under high vacuum, and the residue is chromatographed on silica gel (dichloromethane/methanol 97/3 mixture which contains 1 ml of conc. NH3 ×aq./l). The collected pure fractions are concentrated together in vacuo and dissolved in a little methanol, and saturated ethereal hydrochloric acid (1 ml) and diisopropyl ether are added and the solid which precipitates thereby is filtered off and dried in vacuo. Yield: 200 mg (28%) of the title compound as a colorless solid of melting point >180° (decomposition).

Workup

  1. customThen the excess N-ethylbenzylamine is removed by distillation under high vacuum
  2. customthe residue is chromatographed on silica gel (dichloromethane/methanol 97/3 mixture which contains 1 ml of conc. NH3 ×aq./l)
  3. concentrationThe collected pure fractions are concentrated together in vacuo
  4. dissolutiondissolved in a little methanol, and saturated ethereal hydrochloric acid (1 ml) and diisopropyl ether
  5. additionare added
  6. customthe solid which precipitates
  7. filtrationthereby is filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-15b2229e38f44b4b919c43b1bdb5d9bb
Source dataset
uspto-grants-1997_09
Patent number
US05668131

Reaction notes

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