Diethylcarbamoyl chloride → HCID 13077557, 화합물

HRID 542850

반응식

HRID 542850 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH3:26].C(=O)([O-])[O-].[Na+].[Na+].[CH2:33]([N:35]([CH2:39][CH3:40])[C:36]([Cl:38])=[O:37])[CH3:34]>CC(C)=O>[ClH:38].[ClH:38].[CH2:33]([N:35]([CH2:39][CH3:40])[C:36]([N:23]1[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]2[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]3[C:10]=2[N:9]=[CH:8][CH:7]=[C:6]3[CH3:26])[CH2:25][CH2:24]1)=[O:37])[CH3:34]

참가 물질

5

반응물 3

HCID 6916Diethylcarbamoyl chlorideHCID 10340Sodium CarbonateHCID 130775336-Methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine

생성물 1

HCID 13077557HCID 13077557, 화합물수율 108.1%

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

To a mixture of 2.4 g (0.00673 mole) of 6-methoxy-4-methyl-N-[6-(1-piperazinyl)hexyl]-8-quinolinamine and 1.7 g (0.016 mole) of sodium carbonate in 50 ml of acetone was added a solution of 1.8 g (0.007 mole) of diethylcarbamoylchloride in 20 ml of acetone. The mixture was stirred under gentle reflux for 2 hr, allowed to cool, filtered and concentrated to dryness in vacuo. A solution of the residue in dichloromethane was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Chromatography of the residue over 70 g of silica with 10% methanol in ethyl acetate afforded 2 g of product, Rf=0.3. The material was triturated with 2-propanol containing excess hydrogen chloride. The resulting yellow precipitate was collected, washed with 2-propanol and then ether, dried in vacuo at 52° overnight and air-equilibrated to afford 1.8 g (50%) of the title compound, mp 226°-228° (dec).

후처리

  1. temperatureunder gentle reflux for 2 hr
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationconcentrated to dryness in vacuo
  5. washA solution of the residue in dichloromethane was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-74aafbe616004e3aa64c099d8cfe2ff9
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659708

연결된 노트

불러오는 중…