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

HRID 280375

Reaction equation

HRID 280375 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(N(CC)CC)C.[C:26]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH3:29])([CH3:28])[CH3:27].O=C1N(N(N2CCOC2=O)P(Cl)(N)=O)CCO1.Cl>ClCCl>[C:26]([N:30]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 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 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid (1.3 g, 5 mmols), triethylamine (1.5 ml, 0.01 mol), and N-(tert-butyl)benzylamine (0.93 ml, 5 mmols) in 10 ml dichloromethane, was cooled to 10° C. Then, 1.27 g (5 mmols) of N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride was added, and the reaction mixture was stirred at room temperature for 20 hours. Following acidification with dilute hydrochloric acid, the reaction mixture was filtered and the organic layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure leaving an orange-yellow solid which was recrystallized from anhydrous ethanol. Yield--0.71 g. Mp 195°-197° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customleaving an orange-yellow solid which
  6. customwas recrystallized from anhydrous ethanol
  7. customYield--0.71 g

Sources & evidence

ORD record
ord-077e0e20d447473c971adce20585730c
Source dataset
uspto-grants-1986_05
Patent number
US04588812

Linked notes

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