Hydrochloric Acid → 5-hydroxy-5-(5-phenyl-2-furyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
Reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[NH:17]1[C:25](=[O:26])[C:23](=[O:24])[C:21](=[O:22])[NH:20][C:18]1=[O:19].Cl>CCCCCC.O1CCCC1>[OH:24][C:23]1([C:9]2[O:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:10]=2)[C:21](=[O:22])[NH:20][C:18](=[O:19])[NH:17][C:25]1=[O:26]Participants
Procedure
2-Phenylfuran (5.76 g., 40 mmoles) was combined with 100 ml. of tetrahydrofuran and cooled to -30° C. Butyl lithium in hexane (2.3 M, 19.1 ml.) was added dropwise over 5 minutes, keeping the temperature between -20° and -30° C. The reaction mixture was allowed to warm to room temperature and then recooled to -30° C. Sublimed alloxan (5.96 g., 42 mmoles) in 40 ml. of tetrahydrofuran was added over 5 minutes, again keeping the temperature -20° to -30° C. The reaction mixture was again allowed to warm to room temperature, then recooled to 0° C. and 50 ml. of 1 N hydrochloric acid added portionwise over 2-3 minutes. The quenched reaction mixture was extracted with 100 ml. of ethyl acetate. The extract was filtered through a bed of anhydrous magnesium sulfate, and evaporated to yield 5-hydroxy-5-(5 -phenyl-2-furyl)-2,4,6(1H,3H,5H)pyrimidinetrione [9.4 g., gummy solid, Rf 0.75 (1:1 hexane ethyl acetate/5% acetic acid)] contaminated with starting material (Rf 0.45).
Workup
- customthe temperature between -20° and -30° C
- customrecooled to -30° C
- customthe temperature -20° to -30° C
- temperatureto warm to room temperature
- customrecooled to 0° C.
- customThe quenched reaction mixture
- extractionwas extracted with 100 ml
- filtrationThe extract was filtered through a bed of anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-a21ea7df22f144eb805da9c8d1683efc
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04454320
Reaction notes
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