Dimethyl Sulfate → HCID 18770476, compound

HRID 479325Notes

Reaction equation

HRID 479325 reaction equation
[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]([NH2:19])[C:9]3[C:14]([N:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=1)(=[O:3])[CH3:2].[S:20]([O:25]C)([O:23][CH3:24])(=[O:22])=[O:21]>[N+](C1C=CC=CC=1)([O-])=O>[S:20]([O-:25])([O-:23])(=[O:22])=[O:21].[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]([NH2:19])[C:9]3[C:14]([N+:15]=2[CH3:24])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=1)(=[O:3])[CH3:2].[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:16]2[C:7](=[C:8]([NH2:19])[C:9]3[C:14]([N+:15]=2[CH3:24])=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 18770477HCID 18770477, compound

Product 1

HCID 18770476HCID 18770476, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
140 °C

Procedure

300 cm3 of nitrobenzene are introduced into a 1-dm3 three-necked flask and then 11.2 g (0.0446 mol) of 2-acetamido-9-aminoacridine and 11 cm3 (0.116 mol) of dimethyl sulphate are successively introduced, with stirring. The mixture is then heated at 140° C. for 20 minutes. After cooling, the precipitate obtained is filtered, washed with 20 cm3 of nitrobenzene and six times 20 cm3 of diethyl ether, air-dried and 14.35 g (85%) of 2-acetamido-9-amino-10-methylacridinium sulphate are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate obtained
  3. filtrationis filtered
  4. washwashed with 20 cm3 of nitrobenzene and six times 20 cm3 of diethyl ether
  5. customair-dried

Sources & evidence

ORD record
ord-f5bdb93c1fe14d3487a2994acc75fcfb
Source dataset
uspto-grants-2003_11
Patent number
US06645964B1

Reaction notes

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