Dimethyl Sulfate → HCID 12659858, compound

HRID 2051378Notes

Reaction equation

HRID 2051378 reaction equation
[C:1]([NH:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl[C:22]1C=CC=CC=1.[OH-].[K+].COS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([N:4]([CH3:22])[C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:20])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 7964ChlorobenzeneHCID 14797Potassium HydroxideHCID 76760N-Anthraquinon-1-ylacetamide

Product 1

HCID 12659858HCID 12659858, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-acetylaminoanthraquinone (purity 99.9%, 26.5 g), monochlorobenzene (320 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for 30 minutes while being maintained at 50° C. Then, dimethylsulfuric acid (25.2 g) was dropped at 50° C. over 2 hours. The solution was stirred at 50° C. for 30 minutes, 60° C. for 2 hours and 70° C. for 4 hours, successively. After water (150 g) was added, the solution was stirred for 1 hour while being maintained at 50° C. Then, the same procedure as in Example 3 was carried out to obtain N-acetyl-1-methylaminoanthraquinone (27.9 g, purity 93.6%, yield 93.6%).

Workup

  1. stirringThe solution was stirred at 50° C. for 30 minutes, 60° C. for 2 hours and 70° C. for 4 hours
  2. stirringthe solution was stirred for 1 hour
  3. temperaturewhile being maintained at 50° C

Sources & evidence

ORD record
ord-e292f27f7bc64b29abe51bacf5ea9484
Source dataset
uspto-grants-1991_05
Patent number
US05017713

Reaction notes

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