S-2-naphthylmethyl thioacetimidate → HCID 178465558, compound

HRID 2426282Notes

Reaction equation

HRID 2426282 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][C:15]3[O:18][CH2:19][O:20][C:14]=3[CH:13]=1)[N:6]=[CH:5]2.[C:21](=[NH:35])(SCC1C=CC2C(=CC=CC=2)C=1)[CH3:22]>C(O)C>[O:18]1[C:15]2[CH:16]=[CH:17][C:12]([C:7]3[N:6]=[CH:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:21](=[NH:35])[CH3:22])[CH:3]=4)[N:8]=3)=[CH:13][C:14]=2[O:20][CH2:19]1

Participants

4

Reactant 2

HCID 10856874S-2-naphthylmethyl thioacetimidate2×HCID 441404276-Amino-2-(3,4-methylendioxy-phenyl)quinazoline

Product 1

HCID 178465558HCID 178465558, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension in ethanol (80 ml) of 6-amino-2-(3,4-methylendi-oxy-phenyl)-quinazoline (5 g, 0.019 mol) and S-2-naphthylmethyl thioacetimidate bromidrate (5.63 g, 0.019 mol, prepared as described in Tetrahedron Letters 38, 179-182 (1997), was stirred at r.t. for 24 hrs. Then S-2-naphthylmethyl thioacetimidate bromidrate (2.8 g, 0.010 mol) was added and the mixture was stirred at r.t. for further 24 hrs., then was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was basified with Na2CO3 and extracted with ethyl acetate. The product was extracted with aqueous HCl (0.001 N) for three times. The aqueous layers were collected, basified with Na2CO3 and extracted with ethyl acetate. The organic layer was washed with water and dried over Na2SO4, concentrated under reduced pressure, and then the residue was triturated with diethyl ether. The yellow solid was filtered and dried in vacuum to give the titled product (2.4 g, 42% yield).

Workup

  1. stirringthe mixture was stirred at r.t. for further 24 hrs
  2. concentration, then was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted with ethyl acetate
  5. extractionThe product was extracted with aqueous HCl (0.001 N) for three times
  6. customThe aqueous layers were collected
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customthe residue was triturated with diethyl ether
  12. filtrationThe yellow solid was filtered
  13. customdried in vacuum

Sources & evidence

ORD record
ord-27d787c1f59842f882124675e3d846e4
Source dataset
uspto-grants-2011_06
Patent number
US07968558B2

Reaction notes

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