Dimethyl Sulfate → Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-

HRID 2051380ノート

反応式

HRID 2051380 の反応式
[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][C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1.[CH2:22](C(C)=O)C(C)C.[OH-].[K+].COS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[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]([CH3:22])[C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6497Dimethyl SulfateHCID 7909Methyl Isobutyl KetoneHCID 14797Potassium HydroxideHCID 7730236N-(4-Bromo-9,10-dioxo-9,10-dihydroanthracen-1-YL)acetamide

生成物 1

HCID 80770Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-収率 95.3%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

反応条件

温度
30 °C

実験手順

A mixture of 4-bromo-1-acetylaminoanthraquinone (purity 98%, 35.1 g), methyl isobutyl ketone (500 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for 1 hour while being maintained at 30° C. Dimethylsulfuric acid (25.2 g) was dropped at 30° C. over 2 hours. The mixture was stirred at 30° C. for 1 hour, 40° C. for 2 hours and 50° 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 methyl isobutyl ketone was recovered, 4-bromo-N-acetyl-1-methylaminoanthraquinone (34.8 g, purity 93.6%, yield 91.0%).

後処理

  1. stirringThe mixture was stirred at 30° C. for 1 hour, 40° C. for 2 hours and 50° C. for 4 hours
  2. stirringthe solution was stirred for 1 hour
  3. temperaturewhile being maintained at 50° C
  4. customto obtain
  5. customafter methyl isobutyl ketone was recovered

出典と根拠

ORDレコード
ord-a23538f4e3ee430b98507c4f99c5cedd
出典データセット
uspto-grants-1991_05
特許番号
US05017713

反応ノート

読み込み中…