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

HRID 2050517ノート

反応式

HRID 2050517 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-37e3768e868a416b9d6fe8e989ab6b03
出典データセット
uspto-grants-1991_05
特許番号
US05013737

反応ノート

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