Sodium hydride → 4,5-Dihydro-8-phenyl-5-thioxo-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one

HRID 2050517노트

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HRID 2050517 반응식
[C:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([NH2:18])=[O:17])=[C:11]3[NH:10][CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22]>O1CCCC1>[C:1]1([C:7]2[N:12]3[C:11]4[N:10]([C:21](=[S:22])[NH:18][C:16](=[O:17])[C:15]=4[CH:14]=[N:13]3)[CH2:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 802641,1'-ThiocarbonyldiimidazoleHCID 1358568134,5-Dihydro-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide

생성물 1

HCID 150440804,5-Dihydro-8-phenyl-5-thioxo-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-one수율 41.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A mixture of 7.6 g of 4,5-dihydro-7-phenyl-pyrazolo(1,5-a)pyrimidine-3-carboxamide (prepared as described in Example 25 of commonly assigned U.S. Pat. No. 4,847,256) in 304 ml of dry tetrahydrofuran is stirred and cooled at -78° C., under nitrogen and 2.17 g of sodium hydride (60 percent dispersion in mineral oil) is added. The mixture is stirred at -78° C. for 30 minutes, then 4.84 g of 1,1'-thiocarbonyldiimidazole is added in one portion and the temperature is kept at -78° C. for 2 hours and then is allowed to rise slowly to room temperature. Stirring is continued for 48 hours, and then the reaction mixture is quenched with 500 ml of water and neutralized with 5 percent aqueous hydrochloric acid. A crystalline solid forms which is collected by filtration, triturated with ether, filtered and dried to give 3.2 g of the desired product as white crystals, mp 289-291° C.

후처리

  1. customprepared
  2. waitthe temperature is kept at -78° C. for 2 hours
  3. customto rise slowly to room temperature
  4. stirringStirring
  5. waitis continued for 48 hours
  6. customthe reaction mixture is quenched with 500 ml of water and neutralized with 5 percent aqueous hydrochloric acid
  7. filtrationA crystalline solid forms which is collected by filtration
  8. customtriturated with ether
  9. filtrationfiltered
  10. customdried

출처 및 근거

ORD 기록
ord-37e3768e868a416b9d6fe8e989ab6b03
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05013737

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