Diisopropylethylamine → HCID 14639165, compound

HRID 1460141Notes

Reaction equation

HRID 1460141 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[NH:20][CH2:21][CH2:22][N:23]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[N:23]([C:8]([C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[O:9])[CH2:22][CH2:21][N:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 521532HCID 521532, compoundHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 14639165HCID 14639165, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 2-chloro-3-pyridinylcarbonyl chloride (4.69g) in dichloromethane (25 ml), and add the solution to a stirred, cooled (ice bath) solution of 2-(2-chlorophenyl)methyl-imidazoline (4.30g) and diisopropylethylamine (7.69 ml) and dichloromethane (25 ml). Allow the resulting solution to stir 2 hours, then wash it with water, 1 M sodium bicarbonate solution, and with water. Dry the dichloromethane solution, using sodium sulfate, then filter and evaporate the solvent. Crystallize the residue from ethyl acetate to obtain 2-[(2-chlorophenyl)methyl]-1-[(2-chloro-3-pyridinyl) carbonyl]-4,5-dihydro-1H-imidazole, mp 128.5°-130° C.

Workup

  1. additionadd the solution to a stirred
  2. washwash it with water, 1 M sodium bicarbonate solution
  3. dry with materialDry the dichloromethane solution
  4. filtrationfilter
  5. customevaporate the solvent
  6. customCrystallize the residue from ethyl acetate

Sources & evidence

ORD record
ord-716a27b7fb1741b59f5fd9f2b77d45b6
Source dataset
uspto-grants-1991_12
Patent number
US05070086

Reaction notes

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