Dimethyl Sulfate → 9-Chloro-1-methyl-1,10-phenanthrolinium hydrogen sulfate

HRID 716554

Reaction equation

HRID 716554 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1.[S:16]([O:21]C)([O:19][CH3:20])(=[O:18])=[O:17]>C(OCC)C>[S:16]([O-:21])([OH:19])(=[O:18])=[O:17].[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4]([N:3]=1)=[C:5]1[C:10]([CH:9]=[CH:8][CH:7]=[N+:6]1[CH3:20])=[CH:11][CH:12]=2

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 3551932-Chloro-1,10-phenanthroline

Product 1

HCID 866711149-Chloro-1-methyl-1,10-phenanthrolinium hydrogen sulfateYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Under a stream of argon, to compound (3) (5.2 g; 24.2 mmol), dimethyl sulfate (22.1 g; 175 mmol) was added at room temperature over 10 minutes. The reaction temperature was raised to 120° C. and the resulting reaction mixture was stirred for 1 hour and then cooled to room temperature. Diethyl ether was added thereto and light brown crude crystals which precipitated out were separated by filtration. The obtained crude crystals were washed with a solution of diethyl ether/ethanol=1/1 to 1/2 and dried under reduced pressure to give 6.17 g of the title compound (4).

Workup

  1. customthe resulting reaction mixture
  2. temperaturecooled to room temperature
  3. customlight brown crude crystals which precipitated out
  4. customwere separated by filtration
  5. customThe obtained crude crystals
  6. washwere washed with a solution of diethyl ether/ethanol=1/1 to 1/2
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-22537bab64a748f98f65dfab271d7d10
Source dataset
uspto-grants-2015_11
Patent number
US09187690B2

Linked notes

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