Hydrochloric Acid → Isohexane ethyl acetate

HRID 2306715Notes

Reaction equation

HRID 2306715 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-93ab7b65647d49f0bc55c665bd28eafc
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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