Acetic Anhydride → 5-Methylcarbonyloxy-9-diethylamino-12-acetylbenzo[a]phenoxazine

HRID 1589469

반응식

HRID 1589469 반응식
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]1[C:8](=[CH:9][C:10](=[O:22])[C:11]3[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=31)[O:7]2)[CH3:2].[C:25](OC(=O)C)(=[O:27])[CH3:26].[C:32](OCC)(=[O:34])[CH3:33].C1(C)C=CC=CC=1>[Zn]>[CH3:26][C:25]([O:22][C:10]1[CH:9]=[C:8]2[C:13]([N:14]([C:32](=[O:34])[CH3:33])[C:15]3[C:6]([O:7]2)=[CH:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:23][CH3:24])=[CH:17][CH:16]=3)=[C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=12)=[O:27]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 65182Nile RedHCID 21584019Toluene ethylacetate

생성물 1

HCID 136703955-Methylcarbonyloxy-9-diethylamino-12-acetylbenzo[a]phenoxazine

시약·촉매·용매 1

HCID 23994Zinc촉매

반응 조건

온도
80 °C

실험 절차

A mixture of 10.0 g of 9-diethylaminobenzo[a]phenoxazin-5-one, 75.0 ml of acetic anhydride and 10.0 g of zinc dust was maintained at approximately 80° C. for approximately thirty minutes. After the reaction mixture was cooled to room temperature, the solid present was collected by filtration and it was washed twice, each time with 25.0 ml of acetone. The filtrate and the acetone washes were combined and added slowly to approximately 400.0 ml of water. An oily liquid separated from the water and was extracted from the water with toluene. Subsequently, the toluene solution was washed with water and saturated sodium chloride solution, treated with activated carbon and clarified. The resulting toluene solution was evaporated to dryness. The residue obtained was dissolved in a mixture of ethyl acetate:toluene (2:23::V:V) and purified by passing the solution through a chromatography column packed with silica gel. Fractions 7 through 11 were combined, evaporated to dryness and the residue triturated with hexane to obtain 0.26 g of 5-methylcarbonyloxy-9-diethylamino-12-acetylbenzo[a]phenoxazine (Formula III: R=CH3 ; R2 =R3 =C2H5), a pale brown-colored solid which melted at 64° to 72° C. Significant infrared maxima appeared at 1772 cm-1 (C=O;m) and 1680 cm-1 (C=O;s). Paper treated with an ink formulation of the product produced a strong purple-colored image when traced with an applied voltage stylus.

후처리

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationthe solid present was collected by filtration and it
  3. washwas washed twice
  4. additionadded slowly to approximately 400.0 ml of water
  5. customAn oily liquid separated from the water
  6. extractionwas extracted from the water with toluene
  7. washSubsequently, the toluene solution was washed with water and saturated sodium chloride solution
  8. additiontreated with activated carbon
  9. customThe resulting toluene solution was evaporated to dryness
  10. customThe residue obtained
  11. custompurified
  12. customevaporated to dryness
  13. customthe residue triturated with hexane

출처 및 근거

ORD 기록
ord-a4006a583f2c47bcb105d5381ad67bdf
출처 데이터셋
uspto-grants-1986_02
특허 번호
US04570171

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