S-2-naphthylmethyl thioacetimidate → HCID 178465558, 화합물

HRID 2426282노트

반응식

HRID 2426282 반응식
[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

참가 물질

4

반응물 2

HCID 10856874S-2-naphthylmethyl thioacetimidate2회HCID 441404276-Amino-2-(3,4-methylendioxy-phenyl)quinazoline

생성물 1

HCID 178465558HCID 178465558, 화합물수율 42%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-27d787c1f59842f882124675e3d846e4
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968558B2

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