2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one → 7H-Thiazolo(3,2-b)(1,2,4)triazin-7-one, 3-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)-6-(hydroxymethyl)-
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=O.[OH:20][CH2:21][C:22]1[C:23](=[O:29])[N:24]=[C:25]([SH:28])[NH:26][N:27]=1>C(O)C>[C:11]([C:9]1[CH:10]=[C:5]([C:3]2[N:26]3[N:27]=[C:22]([CH2:21][OH:20])[C:23](=[O:29])[N:24]=[C:25]3[S:28][CH:2]=2)[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]Participants
4
Procedure
14.4 g (0.044 mol) of 2-bromo-1-(3,5-di-tert.butyl-4-hydroxyphenyl)-ethanone (Example 1a1) and 7.0 g (0.044 mol) of 6-hydroxymethyl-3-mercapto-2H-1,2,4-triazin-5-one from step (a1) were heated to boiling for 4 hours in 300 ml of ethanol. The reaction mixture, evaporated under reduced pressure, was dissolved in 300 ml of chloroform and treated with 100 ml of saturated sodium hydrogen carbonate solution. The chloroform phase was finally separated off, dried and evaporated. Chromatography of the crude product over silica gel using ethyl acetate/methanol (99:1) as eluent gave colorless needles.
Workup
- customThe reaction mixture, evaporated under reduced pressure
- dissolutionwas dissolved in 300 ml of chloroform
- additiontreated with 100 ml of saturated sodium hydrogen carbonate solution
- customThe chloroform phase was finally separated off
- customdried
- customevaporated
- customgave colorless needles
Sources & evidence
- ORD record
- ord-e77c3efca0af4110a956c59b4e33d5e3
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04908364
Reaction notes
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