Pyridine → 2-(4-t-Butylazo-4-cyanovaleryloxy)-2'-hydroxybenzophenone

HRID 65894

반응식

HRID 65894 반응식
[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5].N1C=CC=CC=1.CCOCC.[C:28]([N:32]=[N:33][C:34]([C:41]#[N:42])([CH3:40])[CH2:35][CH2:36][C:37](Cl)=[O:38])([CH3:31])([CH3:30])[CH3:29]>CCCCC.O>[C:28]([N:32]=[N:33][C:34]([C:41]#[N:42])([CH3:40])[CH2:35][CH2:36][C:37]([O:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5])=[O:38])([CH3:31])([CH3:29])[CH3:30]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 700382,2'-DihydroxybenzophenoneHCID 152740244-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chloride

생성물 1

HCID 227562192-(4-t-Butylazo-4-cyanovaleryloxy)-2'-hydroxybenzophenone수율 71.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8003Pentane용매

실험 절차

To a solution of 4.68 g. (0.0218 m) of 2,2'-dihydroxybenzophenone and 2.5 ml. of pyridine in 30 ml. of ether in a 4 neck 100 ml. round bottom flask equipped with a thermometer, condenser and magnetic stirring bar was added 5.0 g. (0.0218 m) of 4-t-butylazo-4-cyanovaleryl chloride dropwise with cooling so the temperature did not rise above 25° C. After completion of the addition the reaction mixture was stirred 1/2 hour at room temperature and then diluted with 100 ml. of water. The ether layer was separated, washed consecutively with 5% HCl, water, 10% NaHCO3 solution and saturated sodium chloride solution. The ether was evaporated off leaving a yellow solid. The solid was slurried in pentane, filtered and air dried. The product weighed 6.3 g. (71.2% yield) and decomposed slowly on heating above 80° C. The infrared spectrum of the product was in agreement with the structure of the desired product.

후처리

  1. customround bottom flask equipped with a thermometer, condenser and magnetic stirring bar
  2. additionwas added 5.0 g
  3. customdid not rise above 25° C
  4. additionAfter completion of the addition the reaction mixture
  5. additiondiluted with 100 ml
  6. customThe ether layer was separated
  7. washwashed consecutively with 5% HCl, water, 10% NaHCO3 solution and saturated sodium chloride solution
  8. customThe ether was evaporated off
  9. customleaving a yellow solid
  10. filtrationfiltered
  11. customair dried
  12. temperatureon heating above 80° C

출처 및 근거

ORD 기록
ord-374c8bf7e4504e26b7e3fb98f1f33dde
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04129586

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