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

HRID 2051382노트

반응식

HRID 2051382 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.Cl[C:23]1C=CC=CC=1.[OH-].[K+].CCl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[K+].C(O)(=O)C.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]([CH3:23])[C:19](=[O:21])[CH3:20])=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 6327Methyl ChlorideHCID 7964ChlorobenzeneHCID 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%

시약·촉매·용매 4

HCID 4875Potassium Iodide촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
30 °C

실험 절차

A mixture of 4-bromo-1-acetylaminoanthraquinone (purity 98%, 35.1 g), monochlorobenzene (420 g), tetra-n-butyl ammonium bromide (0.3 g), 96% potassium hydroxide (12.0 g) and potassium iodide (0.5 g) was stirred for 1 hour in an autoclave, while being maintained at 30° C. Then, methyl chloride (10.2 g) was added. The mixture was stirred at 50° C. for 2 hours and 70° C. for 10 hours, successively. After the temperature was lowered to 30° C. and pressure was released, the solution was transferred to a flask by adding water (200 g), and then acetic acid (1.2 g) was added thereto. The aqueous phase had pH of 7. After monochlorobenzene was recovered by heating, the solution was cooled down to 50° C. and filtered. The solid material was washed and dried to obtain 4-bromo-N-acetyl-1-methylaminoanthraquinone (34.7 g, purity 92.9%, yield 90.0%).

후처리

  1. stirringThe mixture was stirred at 50° C. for 2 hours and 70° C. for 10 hours
  2. customwas lowered to 30° C.
  3. customthe solution was transferred to a flask
  4. customAfter monochlorobenzene was recovered
  5. temperatureby heating
  6. temperaturethe solution was cooled down to 50° C.
  7. filtrationfiltered
  8. washThe solid material was washed
  9. customdried

출처 및 근거

ORD 기록
ord-f7f17469e4a945f98377f36a08edbf51
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05017713

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