Dimethylformamide → 5-Ureidoindolin-2-one

HRID 2213670Notes

Reaction equation

HRID 2213670 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

HCID 6228DimethylformamideHCID 70696Trimethylsilyl isocyanateHCID 27732135-Amino-2-oxindole

Product 1

HCID 219578045-Ureidoindolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customA tan-colored solid formed which
  2. customwas isolated by filtration
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6fa50aaa7623420ab11d234df0210d7a
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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