Dichloromethane → HCID 53993518, compound

HRID 1639138Notes

Reaction equation

HRID 1639138 reaction equation
NCC[CH2:4][CH:5]([C:7]1[CH:21]=[CH:20][C:10]2[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[NH:13][C:9]=2[CH:8]=1)[CH3:6].ClCCl.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28].[CH2:31]([N:33](CC)CC)C>>[CH3:25][N:26]([CH3:30])[C:27]([NH:33][CH2:31][C:5]([C:7]1[CH:21]=[CH:20][C:10]2[N:11]=[C:12]([C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[NH:13][C:9]=2[CH:8]=1)([CH3:6])[CH3:4])=[O:28]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 54303402HCID 54303402, compound

Product 1

HCID 53993518HCID 53993518, compound

Procedure

To 0.25 g. 5-(2-aminoethylpropan-2-yl)-2-(4-pyridinyl)-benzimidazole (prepared in Example 1) in 6 ml. dichloromethane is added, with ice cooling, 0.13 ml. triethylamine and 0.1 g. N,N-dimethylcarbamic acid chloride. The reaction mixture is stirred for 20 hours at ambient temperature, the solvent is then removed in a vacuum, the residue is digested with water and the product is filtered off with suction and purified by filtration over a short column of silica gel (elution agent dichloromethane containing 5% methanol). The eluate is evaporated to dryness and the residue is crystallised from ethyl acetate. There is obtained 0.15 g. of the title compound; m.p. 136°-138° C.

Workup

  1. customthe solvent is then removed in a vacuum
  2. filtrationthe product is filtered off with suction
  3. filtrationpurified by filtration over a short column of silica gel (elution agent dichloromethane containing 5% methanol)
  4. customThe eluate is evaporated to dryness
  5. customthe residue is crystallised from ethyl acetate
  6. customThere is obtained 0.15 g

Sources & evidence

ORD record
ord-467f8499a2a848e6b9741d04f234fcdf
Source dataset
uspto-grants-1989_11
Patent number
US04882342

Reaction notes

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