Acetic Acid → HCID 18953495, compound

HRID 1491616Notes

Reaction equation

HRID 1491616 reaction equation
CC(C)([O-])C.[K+].Cl[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[N+:24]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])#[C-:25].C(O)(=O)C>CN(C=O)C>[O:21]1[CH2:22][CH2:23][N:18]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]3[CH:25]=[N:24][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:8]3[N:17]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 533707Ethyl isocyanoacetateHCID 23384664-(2-chloroquinazolin-4-yl)morpholineHCID 23665647Potassium tert-butoxide

Product 1

HCID 18953495HCID 18953495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of potassium t-butoxide (2.1 g, 19 mmol) in dry DMF (15 ml) was added during 15 min. at 0°-5° C. to a stirred solution of 2-chloro-4-morpholino-quinazoline (3.0 g, 12 mmol) and ethyl isocyanoacetate (2.1 g, 19 mmol) in dry DMF (40 ml). The mixture was stirred at room temperature for 2 hours. Then glacial acetic acid (2 ml) was added and the solvent was evaporated in vacuo. The residue was triturated with a mixture of water (50 ml) and ethyl acetate (10 ml) giving the title compound as a pale yellow precipitate. The product was collected by filtration and rinsed with water and ethyl acetate and dried. Yield 3.6 g (91%), m.p. approx. 165° C., resolidifies to give crystals melting at 195.5°-196.5° C.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was triturated with a mixture of water (50 ml) and ethyl acetate (10 ml)

Sources & evidence

ORD record
ord-8bb983e55f064cd5ae0487818c5f8f30
Source dataset
uspto-grants-1994_12
Patent number
US05371080

Reaction notes

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