Hydrochloric Acid → N-(4-cyanobenzoyl)-N'-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)-hydrazine

HRID 2259816

반응식

HRID 2259816 반응식
CC1(C)CCC(C)(C)C2C=C(C(O)=O)C=CC1=2.S(Cl)(Cl)=O.Cl.NN.[CH3:25][C:26]1([CH3:42])[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[C:32]2[CH:31]=[C:30]([C:38]([NH:40][NH2:41])=[O:39])[CH:29]=[CH:28][C:27]1=2.[C:43]([C:45]1[CH:53]=[CH:52][C:48]([C:49](Cl)=[O:50])=[CH:47][CH:46]=1)#[N:44]>C1(C)C=CC=CC=1.C(O)(C)C.O1CCCC1.CCOCC.O>[C:43]([C:45]1[CH:53]=[CH:52][C:48]([C:49]([NH:41][NH:40][C:38]([C:30]2[CH:29]=[CH:28][C:27]3[C:26]([CH3:42])([CH3:25])[CH2:35][CH2:34][C:33]([CH3:36])([CH3:37])[C:32]=3[CH:31]=2)=[O:39])=[O:50])=[CH:47][CH:46]=1)#[N:44]

참가 물질

12

반응물 6

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 24386Thionyl ChlorideHCID 801724-Cyanobenzoyl chlorideHCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acidHCID 190015635,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbohydrazide

생성물 1

HCID 14726546N-(4-cyanobenzoyl)-N'-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)-hydrazine

시약·촉매·용매 5

HCID 962Water용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

23.2 g (0.1 mole) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxylic acid and 18 g (0.15 mole) of thionyl chloride in 75 ml of toluene were heated until hydrogen chloride gas was no longer formed. Thereafter, the mixture was evaporated down, toluene was added several times and the mixture was evaporated down again to remove residual thionyl chloride. The residue was dissolved in 75 ml of isopropanol and added dropwise at from -10° to -15° C. to a solution of 7.4 g (0.23 mole) of hydrazine in 200 ml of isopropanol. The mixture was stirred for 15 minutes at -10° C., 150 ml of water and 50 ml of ether were added and the mixture was stirred again vigorously. The mixture was left to stand overnight, after which the solid was filtered off and the filtrate was extracted with water/ether. The organic phase was washed with water, dried over sodium sulfate and evaporated down. 19.7 g (0.08 mole) of the 5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxylic hydrazide remaining as the residue were dissolved in 100 ml of dry tetrahydrofuran. A solution of 13.5 (0.088 mole) of 4-cyanobenzoyl chloride in 100 ml of tetrahydrofuran was added dropwise at 0° C. The stirred reaction mixture was allowed to reach room temperature in the course of 45 minutes. It was poured onto water, and the precipitated solid was filtered off, washed with ethanol and dried to give 16.4 g of N-(4-cyanobenzoyl)-N'-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthoyl)-hydrazine of melting point 274°-277° C.

후처리

  1. customno longer formed
  2. customThereafter, the mixture was evaporated down
  3. additiontoluene was added several times
  4. customthe mixture was evaporated down again
  5. customto remove residual thionyl chloride
  6. dissolutionThe residue was dissolved in 75 ml of isopropanol
  7. stirringthe mixture was stirred again vigorously
  8. waitThe mixture was left
  9. waitto stand overnight
  10. filtrationafter which the solid was filtered off
  11. extractionthe filtrate was extracted with water/ether
  12. washThe organic phase was washed with water
  13. dry with materialdried over sodium sulfate
  14. customevaporated down
  15. customThe stirred reaction mixture
  16. customto reach room temperature in the course of 45 minutes
  17. additionIt was poured onto water
  18. filtrationthe precipitated solid was filtered off
  19. washwashed with ethanol
  20. customdried

출처 및 근거

ORD 기록
ord-4798587363f54de6b713acc5747489b7
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05475017

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