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

HRID 280374

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-cf5698ff7a884e97b278358b34d4f565
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588812

Linked notes

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