Catechol → 5,10-Dihydrophenazine

HRID 1066396

반응식

HRID 1066396 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[C:9]1([C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)O)O>O>[CH:4]1[C:3]2[NH:8][C:11]3[C:9](=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

4

반응물 2

HCID 289CatecholHCID 7243O-Phenylenediamine

생성물 1

HCID 3453305,10-Dihydrophenazine수율 101.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
170 °C

실험 절차

To a 12 L Morton flask is charged 702 g 1,2-diaminobenzene and 2.1 Kg catechol (3 equivalents based on 1,2-diaminobenzene). Heat is applied by a heating mantle, and at the end of 30 minutes, all materials are melted and the temperature has risen to 90° C. Over the next 40 minutes, the temperature is increased to ca. 170° C. The temperature is maintained in the range of 151° C. to 187° C. over a 4½ day period. The reaction mixture is cooled to 80° C. and 8 L deionized water added over 30 minutes. The mixture is allowed to cool to room temperature overnight, and a filter candle used to remove water. A further 8 L water is added and heated to 70° C., cooled to 40° C., and the water again removed. A further wash with 8 L water is again performed, with the wash temperature lowered only to 60° C. during removal of water. The product is filtered on a filter funnel and air dried for 30 minutes to yield ca. 1200 g of moist 5,10-dihydrophenazine containing approximately 20% water. Yield of dry 5,10-dihydrophenazine is 960 g (68% of theory, based on 1,2-diaminobenzene).

후처리

  1. temperatureHeat
  2. customat the end of 30 minutes
  3. customhas risen to 90° C
  4. temperatureThe temperature is maintained in the range of 151° C. to 187° C. over a 4½ day period
  5. temperatureThe reaction mixture is cooled to 80° C.
  6. additionadded over 30 minutes
  7. temperatureto cool to room temperature overnight
  8. customto remove water
  9. additionA further 8 L water is added
  10. temperatureheated to 70° C.
  11. temperaturecooled to 40° C.
  12. customthe water again removed
  13. washA further wash with 8 L water
  14. customlowered only to 60° C. during removal of water
  15. filtrationThe product is filtered on a filter funnel
  16. customair dried for 30 minutes

출처 및 근거

ORD 기록
ord-6ad28f9f658f4a0d863582f876b0516c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06242602B1

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