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

HRID 2050517Notes

Reaction equation

[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

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-37e3768e868a416b9d6fe8e989ab6b03
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013737

Reaction notes

Loading…