Triethylamine → HCID 178441839, compound

HRID 1656114Notes

Reaction equation

HRID 1656114 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C([N:14]([CH2:17][CH3:18])CC)C.[C:19](Cl)(=O)[CH2:20][CH2:21]CC.CCOC(C)=O.CCCCCC>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:18]([C:17]1[NH:1][C:2]2[C:3]([C:4](=[O:6])[N:14]=1)=[CH:7][C:8]([CH3:11])=[CH:9][CH:10]=2)[CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 762552-Amino-5-methylbenzoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 178441839HCID 178441839, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3.0 g (20 mmol) of 2-amino-5-methylbenzoic acid in 20 mL of dry DMF at 0° C. was added 200 mg of DMAP followed by 6.07 g (60 mmol) of triethyl amine and 5.02 g (40 mmol) of valeryl chloride. The resulting mixture was stirred at 0° C. for 30 minutes. The mixture was heated to 110° C. and monitored by TLC for the formation of the intermediate quinoxazolone (rf=0.8, 40% EtOAc/hexane). Following complete formation of the intermediate 10 g (100 mmol) of NH4CO3 was added cautiously. Heating was continued to ensure consumption of the quinoxazolone and formation of the polar (rf=0.4, 40% EtOAc/hexane) quinazolin-4(1H-one. The reaction mixture was concentrated in vacuo and the residue was taken up in 50 mL of ether and 50 mL of water. The mixture was filtered and the filtrate discarded after washing the residue with 20 mL of water. The residue was recrystallized from MeOH to give 1.07 g (5 mmol) of a white crystaline solid. 25% yield overall. 1H-NMR (CDCl3): 0.94 (t, 3H, J=6.7 Hz), 1.50 (m, 2H), 1.83 (m, 2H), 2.49 (s, 3H), 2.78 (t, 2H), 7.60 (m, 2H), 8.05 (m, 1H). Anal (C13H16N2O), C, H, N.

Workup

  1. temperatureThe mixture was heated to 110° C.
  2. additionwas added cautiously
  3. temperatureHeating
  4. customconsumption of the quinoxazolone and formation of the polar (rf=0.4, 40% EtOAc/hexane) quinazolin-4(1H-one
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. filtrationThe mixture was filtered
  7. washafter washing the residue with 20 mL of water
  8. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-9e9f62b0f2ad4005bac8a6c16c2f9527
Source dataset
uspto-grants-1993_10
Patent number
US05252574

Reaction notes

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