Cyanogen Bromide → HCID 86655411, compound

HRID 2190498Notes

Reaction equation

HRID 2190498 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[NH2:23])[O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=1.[N:24]#[C:25]Br>O1CCCC1.C(OCC)(=O)C>[NH2:24][C:25]1[NH:1][C:2]2[CH:3]=[C:4]([O:5][C:6]3[CH:7]=[C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][CH:11]=3)[CH:20]=[CH:21][C:22]=2[N:23]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 86655410Tert-butyl [3-(3,4-diaminophenoxy)phenyl]carbamate

Product 1

HCID 86655411HCID 86655411, compoundYield 135%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [3-(3,4-diaminophenoxy)phenyl]carbamate (3.00 g, 9.51 mmol) in tetrahydrofuran (150 mL) was added cyanogen bromide (2.93 g, 27.7 mmol), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate (300 mL), washed with saturated aqueous sodium hydrogencarbonate solution (100 mL×2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated to give the title compound (4.37 g) as a brown solid.

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate solution (100 mL×2) and saturated brine (100 mL)
  2. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-559fdf3736054b40a7894b02a1f3417e
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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