Dimethyl Sulfate → 7-Chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate

HRID 649148Notes

Reaction equation

HRID 649148 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[C:14]([CH2:15][N:16]([CH3:18])[CH3:17])=[C:13]([CH3:19])[N:12]=[C:7]12.[S:20]([O:25]C)([O:23][CH3:24])(=[O:22])=[O:21]>O1CCCC1>[CH3:24][O:23][S:20]([O-:25])(=[O:22])=[O:21].[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]1[C:14]([CH2:15][N+:16]([CH3:24])([CH3:18])[CH3:17])=[C:13]([CH3:19])[N:12]=[C:7]12

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 138218297-Chloro-3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline

Product 1

HCID 138218647-Chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7-chloro-3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline (3.4 g) in tetrahydrofuran (30 ml) was added dropwise to a solution of dimethyl sulfate (3.5 ml) in tetrahydrofuran (20 ml) with ice-cooling and stirring. After being stirred for 2 hours under the same conditions, the resulting precipitates were collected by filtration and washed with tetrahydrofuran and then ethanol to give 7-chloro-2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (4.4 g).

Workup

  1. temperaturecooling
  2. stirringAfter being stirred for 2 hours under the same conditions
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-f685f738a5e64f17819daf143d35faf4
Source dataset
uspto-grants-1988_04
Patent number
US04738967

Reaction notes

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