N-(1-Hydroxy-2-methylpropan-2-yl)thiourea → 4-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile
Reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7]([NH2:9])=[S:8])([CH3:5])[CH3:4].Br[CH2:11][C:12]([C:14]1[CH:15]=[C:16]([C:20]#[N:21])[N:17]([CH3:19])[CH:18]=1)=O>C(O)C>[OH:1][CH2:2][C:3]([NH:6][C:7]1[S:8][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]([C:20]#[N:21])[N:17]([CH3:19])[CH:18]=2)[N:9]=1)([CH3:5])[CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(2-Hydroxy-1,1-dimethylethyl)thiourea (0.75 g, 5 mmol), prepared in step 2 of Example 52, was added to 4-(2-bromo-acetyl)-1-methyl-1H-pyrrole-2-carbonitrile (1.15 g, 5 mmol), prepared in the previous step, in ethanol (20 mL) and the mixture was heated under reflux. After 2 h, the reaction was cooled to room temperature, the precipitate was collected, washed with ethanol, suspended in water and made basic with a 1 N sodium carbonate solution. The mixture was extracted with ethyl acetate, the organic layer was then washed with a 1 N sodium carbonate solution, water, dried (anhydrous MgSO4) and evaporated to afford 4-[2-(2-hydroxy-1,1-dimethyl-ethylamino)-thiazol-4-yl]-1-methyl-1H-pyrrole-2-carbonitrile (0.92 g, 67%), which was used without further characterization.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux
- customthe precipitate was collected
- washwashed with ethanol
- extractionThe mixture was extracted with ethyl acetate
- washthe organic layer was then washed with a 1 N sodium carbonate solution, water
- dry with materialdried (anhydrous MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-49bba87b623a4b5f92c80ff367c5de80
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618990B2
Reaction notes
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