Phenol → (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic Acid Phenyl Ester

HRID 280373

Reaction equation

HRID 280373 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:17].O=C1N(N(N2CCOC2=O)P(Cl)(N)=O)CCO1.[C:36]1(O)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl.O>[C:36]1([O:17][C:16](=[O:18])[CH:15]=[C:3]2[S:4][C:5]3=[N:6][C:7]4[C:12]([CH2:13][N:14]3[C:2]2=[O:1])=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 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 54508713(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic Acid Phenyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.30 g (5 mmols) (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid, 1.27 g (5 mmols) N,N-bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride, 0.49 g (5.2 mmols) phenol, and 1.10 g (10 mmols) triethylamine, in 10 ml dichloromethane was stirred at room temperature, under nitrogen atmosphere for 18 hours. Then, 10 ml of water (made slightly basic with sodium bicarbonate) were added. The precipitate was filtered of and the filtrate was dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The residual orange-yellow solid was recrystallized from anhydrous ethanol. Yield--0.62 g. Mp 194°-195° C.

Workup

  1. additionwere added
  2. filtrationThe precipitate was filtered of and the filtrate
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe residual orange-yellow solid was recrystallized from anhydrous ethanol
  6. customYield--0.62 g

Sources & evidence

ORD record
ord-9bc3fb30f72f49fa81b82afc6e70df78
Source dataset
uspto-grants-1986_05
Patent number
US04588812

Linked notes

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