Hydrochloric Acid → N-tert-butyl-N-benzyl(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide

HRID 280371

Reaction equation

HRID 280371 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.[C:19]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:22])([CH3:21])[CH3:20].O=C1N(N(N2CCOC2=O)P(Cl)(N)=O)CCO1.Cl>ClCCl.C(N(CC)CC)C>[C:19]([N:23]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[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)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 76908N-(1,1-Dimethylethyl)benzenemethanamineHCID 21249497N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chlorideHCID 54200705(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid

Product 1

HCID 53873445N-tert-butyl-N-benzyl(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
10 °C

Procedure

The compound, (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid (compound IIIa), triethylamine, and N-(tert-butyl)benzylamine, in relative molar amounts of 1, 2, and 1, respectively, are dissolved in dichloromethane, and the solution is cooled to 10° C. The compound, N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride, (relative molar amount, 1) is added to the reaction mixture, which is then stirred at about 25° C. for about 2 hours. Following acidification with dilute hydrochloric acid, the reaction mixture is filtered, and the organic phase is washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure, leaving the N-tert-butyl-N-benzyl(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide as a solid. The N-tert-butyl-N-benzyl(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide (compound VI) is then recrystallized from anhydrous ethanol. Replacement of (3-oxo-5H-thiazolo[2,3-b]2(3H)-ylidene)acetic acid with a derivative thereof in which a nuclear hydrogen of the benzene ring has been substituted with lower alkyl, alkoxy, halogen, trifluoromethyl, NO2 or NH2, results in the formation of the corresponding derivative of N-tert-butyl-N-benzyl(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetamide.

Workup

  1. filtrationthe reaction mixture is filtered
  2. washthe organic phase is washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bb506b7391854d1f9320e8d8c1d9abf5
Source dataset
uspto-grants-1986_05
Patent number
US04588812

Linked notes

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