Methyl iodide → HCID 15176764, compound

HRID 2051385Notes

Reaction equation

HRID 2051385 reaction equation
[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:31]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[Br:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([N:18]([CH3:31])[S:19]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 19833420HCID 19833420, compound

Product 1

HCID 15176764HCID 15176764, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 4-bromo-1-p-toluenesulfonylaminoanthraquinone (purity 98%, 46.5 g), monochlorobenzene (550 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for 1 hour at 30° C. and methyl iodide (28.4 g) was added thereto at 30° C. over 2 hours. A mixture was stirred at 30° C. for 30 minutes and 40° C. for 3 hours, successively. Then, the same aftertreatment as in Example 3 was effected to obtain 4-bromo-N-p-toluenesulfonyl-1-methylaminoanthraquinone (46.9 g, purity 92.5%, yield 92.3%).

Workup

  1. waitat 30° C. over 2 hours
  2. stirringA mixture was stirred at 30° C. for 30 minutes and 40° C. for 3 hours

Sources & evidence

ORD record
ord-d640ba3e80854158803f588576a0d680
Source dataset
uspto-grants-1991_05
Patent number
US05017713

Reaction notes

Loading…