Triethylamine → N-(8-PHENYL-4,5-DIHYDRO-THIAZOLO[4,5-h]QUINAZOLIN-2-YL)-PROPIONIC ACID AMIDE

HRID 1517670Notes

Reaction equation

HRID 1517670 reaction equation
[C:1]1([C:7]2[N:16]=[CH:15][C:14]3[CH2:13][CH2:12][C:11]4[N:17]=[C:18]([NH2:20])[S:19][C:10]=4[C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>ClCCl>[C:1]1([C:7]2[N:16]=[CH:15][C:14]3[CH2:13][CH2:12][C:11]4[N:17]=[C:18]([NH:20][C:28](=[O:31])[CH2:29][CH3:30])[S:19][C:10]=4[C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 577412698-PHENYL-4,5-DIHYDRO-THIAZOLO[4,5-h]QUINAZOLIN-2-YLAMINE

Product 1

HCID 57741208N-(8-PHENYL-4,5-DIHYDRO-THIAZOLO[4,5-h]QUINAZOLIN-2-YL)-PROPIONIC ACID AMIDE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.3 g (1.1 mmol) of the compound obtained in Example 71 are suspended in 15 ml dichloromethane, combined with 0.4 ml (2.5 mmol) triethylamine and gently refluxed. 0.2 ml (2.3 mmol) propionic acid chloride are added and the mixture is refluxed for 5 hours with stirring. After cooling to ambient temperature the reaction solution is washed with sodium hydrogen carbonate and water, dried and evaporated to dryness. The residue is stirred with diethyl ether and suction filtered. Yield: 0.2 g (m.p.: 274-275° C.)

Workup

  1. temperaturegently refluxed
  2. temperaturethe mixture is refluxed for 5 hours
  3. washis washed with sodium hydrogen carbonate and water
  4. customdried
  5. customevaporated to dryness
  6. stirringThe residue is stirred with diethyl ether and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-00e2dc7cff544f5cb58671ee842f9590
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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