Thionyl Chloride → HCID 178499149, compound

HRID 1808348Notes

Reaction equation

HRID 1808348 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:12]([CH2:16][C:17]1[N:18]=[CH:19][NH:20][C:21]=1[C:22]([O:24][CH3:25])=[O:23])[CH2:13][CH2:14]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:5]([N:12]([CH2:16][C:17]1[N:18]=[CH:19][NH:20][C:21]=1[C:22]([O:24][CH3:25])=[O:23])[CH2:13][CH2:14][Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178499151HCID 178499151, compound

Product 1

HCID 178499149HCID 178499149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

Thionyl chloride (0.5 ml, 4 equiv.) was added to a solution of methyl 4-((benzyl(2-hydroxyethyl)amino)methyl)-1H-imidazole-5-carboxylate (1.7 mmol, 1 equiv.) in DCM (10 ml), and the mixture was stirred for 16 h at 45° C. The reaction mixture was cooled to 25° C. and concentrated in vacuo. The residue was taken up in acetonitrile, the solvent was removed, and the residue was dried for 24 h in vacuo. The desired product was thus obtained in the form of a white solid. This was used in the following stage without further purification. Yield: quantitative

Workup

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. concentrationconcentrated in vacuo
  3. customthe solvent was removed
  4. customthe residue was dried for 24 h in vacuo

Sources & evidence

ORD record
ord-b390ba2a62af431687ebf2ec6d680ff5
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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