Ammonia → HCID 13173170, compound
Reaction equation
[NH2:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.[C:7]([C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[C:14](=O)[CH2:15]Br)([CH3:10])([CH3:9])[CH3:8].N.O>C(C(C)=O)C.C(O)C>[C:22]([C:19]1[CH:18]=[C:13]([C:14]2[N:1]=[C:2]3[N:6]([CH:15]=2)[CH2:5][CH2:4][S:3]3)[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:20]=1[OH:21])([CH3:25])([CH3:24])[CH3:23]Participants
Procedure
In 300 ml of methyl ethyl ketone was dissolved 10.2 g of 2-amino-2-thiazoline and after adding 32.7 g of 3,5-di-tert-butyl-4-hydroxyphenacyl bromide was added portionwise to the solution followed by stirring for 30 minutes at room temperature, the resultant mixture was refluxed for one hour. Then, the solvent was distilled off under reduced pressure, the crystals thus formed were dissolved in 200 ml of ethanol, and the solution was refluxed for 4 hours. The reaction mixture was basified with the addition of aqueous ammonia and then 200 ml of water was added to the reaction mixture to precipitate crude crystals, which were recovered by filtration and recrystallized from ethanol to provide 23.5 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole.
Workup
- additionwas added portionwise to the solution
- distillationThen, the solvent was distilled off under reduced pressure
- customthe crystals thus formed
- temperaturethe solution was refluxed for 4 hours
- customto precipitate crude crystals, which
- filtrationwere recovered by filtration
- customrecrystallized from ethanol
Sources & evidence
- ORD record
- ord-0df69fc9238143509d8a77b012eafff6
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04636516
Reaction notes
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