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

HRID 2051377ノート

反応式

HRID 2051377 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.[OH-].[K+].[CH3:24]OS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.ClC1C=CC=CC=1.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]([CH3:24])[C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

参加物

8

反応物 3

HCID 6497Dimethyl SulfateHCID 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 95.8%

試薬・触媒・溶媒 4

HCID 176Acetic Acid触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 7964Chlorobenzene溶媒2 回

反応条件

温度
30 °C

実験手順

A mixture of 4-bromo-1-acetylaminoanthraquinone (purity 98%, 35.1 g), monochlorobenzene (420 g), tetra-n-butyl ammonium bromide (0.3 g) and 96% potassium hydroxide (12.0 g) was stirred for one 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 30 minutes, 40° C. for 2 hours and 50° C. for 4 hours, successively. After water (200 g) was added, the solution was stirred for 1 hour while being maintained at 50° C. pH of the aqueous phase was 10 or higher. After acetic acid (0.5 g) was added for neutralization (pH of the aqueous phase being 7), monochlorobenzene was recovered by heating. After being cooled down to 50° C., the solution was filtered. A solid material was washed and dried to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (35.0 g, purity 94.0%, yield 91.9%).

後処理

  1. stirringThe mixture was stirred at 30° C. for 30 minutes, 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. pH of the aqueous phase
  4. customwas recovered
  5. temperatureby heating
  6. temperatureAfter being cooled down to 50° C.
  7. filtrationthe solution was filtered
  8. washA solid material was washed
  9. customdried

出典と根拠

ORDレコード
ord-d04364ea92af4144b57991ed197505f3
出典データセット
uspto-grants-1991_05
特許番号
US05017713

反応ノート

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