Ethyl Bromide → Carbamic acid, N-ethyl-, 2-((2-cyanoethyl)phenylamino)ethyl ester

HRID 25916

반응식

HRID 25916 반응식
[O-:1][C:2]#[N:3].[K+].S1(CCCC1)(=O)=O.Br[CH2:13][CH3:14].[C:15]([CH2:17][CH2:18][N:19]([CH2:26][CH2:27][OH:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)#[N:16]>O>[C:15]([CH2:17][CH2:18][N:19]([CH2:26][CH2:27][O:28][C:2](=[O:1])[NH:3][CH2:13][CH3:14])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)#[N:16]

참가 물질

6

반응물 4

HCID 6332Ethyl Bromide2회HCID 31347Sulfolane2회HCID 113349Propanenitrile, 3-[(2-hydroxyethyl)phenylamino]-HCID 11378442Potassium cyanate

생성물 1

HCID 113132Carbamic acid, N-ethyl-, 2-((2-cyanoethyl)phenylamino)ethyl ester

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

Into a 500 ml. three-necked round-bottomed flask equipped with thermometer, stirrer, reflux condenser, and dropping funnel are placed 40 g. (0.493 mole) of potassium cyanate and 250 ml. of sulfolane (tetrahydrothiophene-1,1-dioxide). This mixture is heated with stirring to 90° C. by means of an oil bath. Bromoethane (95 g., 0.8 mole) is then added dropwise to the mixture over a 1.5 hour period. The temperature of the reaction mixture drops to 75° C. during the addition of bromoethane. A solution of 50 g. (0.228 mole, 86.5%) N-(2-cyanoethyl)-N-(2-hydroxyethyl) aniline in 50 ml. of sulfolane is added, and heating of the resulting mixture is continued at 90° C. for three hours. The reaction mixture is cooled to room temperature and then poured into 2 liters of cold water. The mixture is agitated for 0.5 hour, and the two resulting layers separated. TLC of the organic layer in 4:1 benzene:acetone shows only a trace of starting material. The infrared spectrum of the product of the above formula shows absorptions at 3370, 2250, 1915, 1680, and 596 cm-1.

후처리

  1. customthree-necked round-bottomed flask equipped with thermometer, stirrer
  2. temperaturereflux condenser
  3. temperatureThis mixture is heated
  4. temperatureheating of the resulting mixture
  5. temperatureThe reaction mixture is cooled to room temperature
  6. stirringThe mixture is agitated for 0.5 hour
  7. customthe two resulting layers separated

출처 및 근거

ORD 기록
ord-a0a3b9ed9b4f48ae977754f28469faf6
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147716

연결된 노트

불러오는 중…