Dimethyl Sulfate → HCID 12659858, compound

HRID 2051379Notes

Reaction equation

HRID 2051379 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].[C:21]1(C)C(C)=CC=CC=1.[OH-].[K+].COS(=O)(=O)OC>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([N:4]([CH3:21])[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 7237O-XyleneHCID 14797Potassium HydroxideHCID 76760N-Anthraquinon-1-ylacetamide

Product 1

HCID 12659858HCID 12659858, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-acetylaminoanthraquinone (purity 99.9%, 26.5 g), xylene (500 g), tetra-n-butyl ammonium chloride (0.6 g) and 96% potassium hydroxide (12.0 g) was stirred for 1 hour while being maintained at 50° C. Then, dimethylsulfuric acid (25.2 g) was dropped at 50° C. over 2 hours. The mixture was stirred at 50° C. for 30 minutes, 60° C. for 2 hours and 70° C. for 4 hours, successively. After water (250 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 applied to obtain, after xylene was recovered, N-acetyl-1-methylaminoanthraquinone (27.7 g, purity 92.4%, yield 91.7%).

Workup

  1. stirringThe mixture 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
  4. customto obtain
  5. customafter xylene was recovered

Sources & evidence

ORD record
ord-25eb099a6a504c9486c087454403550f
Source dataset
uspto-grants-1991_05
Patent number
US05017713

Reaction notes

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