Benzylamine → N-Benzyl-(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide

HRID 280374

반응식

HRID 280374 반응식
[O:1]=[C:2]1[N:14]2[C:5](=[N:6][C:7]3[C:12]([CH2:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:4][C:3]1=[CH:15][C:16]([OH:18])=O.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(P(C#N)(CC)=O)C.C(N(CC)CC)C>CN(C)C=O.C1C=CC=CC=1.C(OCC)(=O)C>[CH2:19]([NH:26][C:16](=[O:18])[CH:15]=[C:3]1[S:4][C:5]2=[N:6][C:7]3[C:12]([CH2:13][N:14]2[C:2]1=[O:1])=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 13586794DiethylphosphorylcyanideHCID 54200705(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid

생성물 1

HCID 54292886N-Benzyl-(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21583983Benzene ethyl acetate용매

반응 조건

온도
0 °C

실험 절차

To a stirred mixture of (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid (10.5 g, 1.9 mmols) and benzylamine (0.23 g, 2.1 mmols) in 25 ml dimethylformamide at 0° C., was added diethylphosphoryl cyanide (0.28 g, 2.1 mmols) (in dimethylformamide solution), followed by triethylamine (0.41 g, 4.0 mmols). The reaction mixture was stirred for 4 hours at 0° C. and then, at room temperature overnight. The reaction mixture was diluted with benzene-ethyl acetate and washed sequentially with 5% hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic solution was dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to give N-Benzyl-(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide which was recrystallized from ethyl acetate. Yield--0.09 g. Mp 258°-259° C.

후처리

  1. customat room temperature
  2. customovernight
  3. washwashed sequentially with 5% hydrochloric acid, water, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  5. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-cf5698ff7a884e97b278358b34d4f565
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588812

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