Hydrochloric Acid → Isohexane ethyl acetate

HRID 1936786Notes

Reaction equation

HRID 1936786 reaction equation
[CH2:1](OC1C=CC(NC2(N)C3C(=CC=C(C4O[C:28]([CH:31]5[O:35][CH2:34][CH2:33][O:32]5)=CC=4)C=3)N=CN2)=CC=1)[C:2]1[CH:7]=C[CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH3:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1].[C:31]([O:32][CH2:33][CH3:34])(=[O:35])[CH3:28]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178508193HCID 178508193, compound

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-(4-benzyloxy-phenylamino)-(6-(5-(1,3-dioxolan-2-yl)-furan-2-yl)-quinazolin-4-yl)-amine (1.0 g, 2.1 mmol) was dissolved in THF (20 ml) and hydrochloric acid (2N, 10 ml) was added. The reaction was stirred at room temperature for 1 hr. The precipitate which formed was collected by filtration and washed with acetone, then partitioned between ethyl acetate, triethylamine and water. The organic phase was washed with water, dried (magnesium sulphate) and the solvent was removed under vacuum. Trituration with iso-hexane/ethyl acetate gave the product as an orange solid (610 mg, 69%); δH [2H6]-DMSO 10.05 (1H, b, NH), 9.62 (1H, s, CHO), 8.95 (1H, s, 5-H), 8.48 (1H, s, 2-H), 8.24 (1H, d, 7-H), 7.80 (1H, d, 8-H), 7.70 (1H, d, furan 4-H), 7.59 (2H, d, 2′-H, 6′-H), 7.48-7.25 (6H, m, 5×Ph-H, furan 3-H), 7.02 (2H, m, 3′-H, 5′-H), 5.09 (2H, s, CH2); m/z 422 (M+1)+.

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration
  3. washwashed with acetone
  4. custompartitioned between ethyl acetate, triethylamine and water
  5. washThe organic phase was washed with water
  6. dry with materialdried (magnesium sulphate)
  7. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-1b8112abd1fa4504a89a7893d2635041
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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