Bromobenzene → N~2~,N~2~-Diethylquinazoline-2,4-diamine

HRID 1576325

반응식

HRID 1576325 반응식
BrC1C=CC=CC=1.[Li].[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[CH2:18]([N:20]([CH2:23][CH3:24])[C:21]#[N:22])[CH3:19]>O.C(OCC)C>[NH2:13][C:12]1[C:11]2[C:10](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=[C:21]([N:20]([CH2:23][CH3:24])[CH2:18][CH3:19])[N:22]=1

참가 물질

7

반응물 4

HCID 7961BromobenzeneHCID 12050DiethylcyanamideHCID 729132-AminobenzonitrileHCID 3028194Lithium

생성물 1

HCID 345849N~2~,N~2~-Diethylquinazoline-2,4-diamine

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매3회

실험 절차

Under a nitrogen atmosphere 4.7 g. (0.03 mol) of bromobenzene dissolved in 35 ml. of anhydrous diethyl ether, are added to 0.42 g. (0.06 mol) of lithium. To the solution obtained, a solution of 0.03 mol o-aminobenzonitrile in 15 ml. of anhydrous diethyl ether is added dropwise at room temperature. After about 10 minutes, a solution of 0.03 mol diethylcyanamide in 10 ml. of anhydrous diethyl ether is added dropwise. The reaction mixture is then refluxed under the nitrogen atmosphere for 4 hours. The next day the mixture is decomposed by addition of water. The ethereal layer is separated off, washed with water, dried over sodium sulphate and concentrated by evaporation of solvent. Some petroleum ether (boiling range 28°-40°C.) is added to the residue, the solid is filtered off and crystallized from a mixture of methanol and water. 4-Amino-2-diethylaminoquinazoline, m.p. 125°-128°C., is obtained.

후처리

  1. customTo the solution obtained
  2. temperatureThe reaction mixture is then refluxed under the nitrogen atmosphere for 4 hours
  3. customThe ethereal layer is separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation of solvent
  7. additionSome petroleum ether (boiling range 28°-40°C.) is added to the residue
  8. filtrationthe solid is filtered off
  9. customcrystallized from a mixture of methanol and water

출처 및 근거

ORD 기록
ord-912b0dca4fea47cb9ebad674654a8bc1
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03980650

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