Sodium Bicarbonate → N-(2-Benzoyl-6-chloro-1H-indol-3-yl)urea
Reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-:20][C:21]#[N:22].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C:12]([C:3]1[NH:4][C:5]2[C:10]([C:2]=1[NH:1][C:21]([NH2:22])=[O:20])=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 3-amino-2-benzoyl-6-chloroindole (step 1, 60 mg, 0.21 mmol) in acetic acid (10 ml) was added sodium cyanate (14 mg, 0.21 mmol) and the mixture was stirred for 1.5 h at 90° C. After cooling, the mixture was poured into a saturated sodium bicarbonate (50 ml) and extracted with ethyl acetate (40 ml×2), dried (MgSO4) and concentrated. The residual solids were purified by flash column chromatography eluting with hexane/ethyl acetate (1/1) to give 10 mg (15%) of the title compound as yellow solids.
Workup
- temperatureAfter cooling
- extractionextracted with ethyl acetate (40 ml×2)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residual solids were purified by flash column chromatography
- washeluting with hexane/ethyl acetate (1/1)
Sources & evidence
- ORD record
- ord-f247e778d7da4b47b317de92f4946af1
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06277878B1
Reaction notes
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