Dimethylformamide → 5-Ureidoindolin-2-one
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.C[N:13](C)[CH:14]=[O:15].C[Si](N=C=O)(C)C>O1CCCC1>[NH:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2)[C:14]([NH2:13])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-aminoindolin-2-one (8.76, 58.79 mmol) in tetrahydrofuran:dimethylformamide (400 mL:60 mL) was added trimethylsilylisocyanate (10.6 mL, 78.68 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 18 hours. A tan-colored solid formed which was isolated by filtration, washed with ether and dried in vacuo to afford 5-ureidoindolin-2-one (8.5 g).
Workup
- customA tan-colored solid formed which
- customwas isolated by filtration
- washwashed with ether
- customdried in vacuo
Sources & evidence
- ORD record
- ord-6fa50aaa7623420ab11d234df0210d7a
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105563B2
Reaction notes
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