2-Chlorophenol → 2,5-Cyclohexadien-1-one, 2-chloro-4-((4-(diethylamino)-2-methylphenyl)imino)-

HRID 234751

반응식

HRID 234751 반응식
C([O-])([O-])=O.[Na+].[Na+].Cl.[CH2:8]([N:10]([C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([CH3:20])[CH:14]=1)[CH2:11][CH3:12])[CH3:9].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[OH:28]>CO.O.C(O)C>[Cl:21][C:22]1[C:23](=[O:28])[CH:24]=[CH:25][C:26](=[N:17][C:16]2[CH:18]=[CH:19][C:13]([N:10]([CH2:11][CH3:12])[CH2:8][CH3:9])=[CH:14][C:15]=2[CH3:20])[CH:27]=1

참가 물질

7

반응물 3

HCID 72452-ChlorophenolHCID 10340Sodium CarbonateHCID 108623N,N-Diethyltoluene-2,5-diamine hydrochloride

생성물 1

HCID 1096752,5-Cyclohexadien-1-one, 2-chloro-4-((4-(diethylamino)-2-methylphenyl)imino)-수율 90%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 887Methanol용매HCID 962Water용매3회

반응 조건

온도
55 °C

실험 절차

1450 parts K3Fe(CN)6, 595 parts Na2CO3, and 4150 parts water were added to a 12-liter round bottom flask equipped with a mechanical stirrer, thermometer, and addition funnel. The mixture was heated to 55° C. with stirring. A solution of 227 parts 4-(N,N-diethylamino)-2-methylaniline monohydrochloride, 128 parts o-chlorophenol, 1960 parts ethanol, and 2500 parts water was charged to the addition funnel and added dropwise to the stirred, heated solution. After the addition was complete the reaction mixture was maintained at 55° C. with stirring for 20 minutes. The warm mixture was filtered with vacuum and the resulting filter cake was placed in a solution of 296 parts ethanol and 1125 parts water to form a slurry. The dye was isolated by vacuum filtration. This process was repeated two times, first with 296 parts ethanol and 1125 parts water, then with 608 parts methanol. After the final vacuum filtration the filter cake was dried at 40° C. under vacuum for 48 hours. Yield was ~90%. The final product can be recrystallized from ethyl acetate or ethanol.

후처리

  1. customequipped with a mechanical stirrer
  2. additionthermometer, and addition funnel
  3. additionadded dropwise to the stirred
  4. temperatureheated solution
  5. additionAfter the addition
  6. temperaturewas maintained at 55° C.
  7. stirringwith stirring for 20 minutes
  8. filtrationThe warm mixture was filtered with vacuum
  9. filtrationthe resulting filter cake
  10. customto form a slurry
  11. customThe dye was isolated by vacuum filtration
  12. filtrationAfter the final vacuum filtration the filter cake
  13. customwas dried at 40° C. under vacuum for 48 hours
  14. customThe final product can be recrystallized from ethyl acetate or ethanol

출처 및 근거

ORD 기록
ord-084edde874f649ec9ddd0f2e85d1e229
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596025

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