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

HRID 2051380

반응식

HRID 2051380 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

반응 조건

온도
30 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a23538f4e3ee430b98507c4f99c5cedd
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05017713

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