Water → HCID 58118506, compound

HRID 1182851Notes

Reaction equation

HRID 1182851 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([Br:11])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([NH2:14])=[O:13].[O:15]=[C:16](Cl)OC(Cl)(Cl)Cl.O>O1CCOCC1>[Br:11][C:6]1[C:5]2[NH:4][C:3]3[C:12](=[O:13])[NH:14][C:16](=[O:15])[NH:1][C:2]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 58118555HCID 58118555, compound

Product 1

HCID 58118506HCID 58118506, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8.0 g (32 mmol) 3-amino-7-bromo-1H-indole-2-carboxylic acid amide was suspended in 50 ml dioxan, and refluxed after the addition of 3.8 ml (32 mmol) diphosgene for 3 h. Having cooled down to room temperature, 20 ml water was carefully added and the precipitate was then sucked off. 9.0 g (32%) 6-bromo-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione was obtained. ESI-MS [m/z]: 278, 280 [M−H]−

Workup

  1. temperaturerefluxed

Sources & evidence

ORD record
ord-0ce45bf5bb244c22886042074070ef40
Source dataset
uspto-grants-2014_03
Patent number
US08664233B2

Reaction notes

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