Cyanogen Bromide → Cyanamide, (5-chloro-2-nitrophenyl)(2-methylpropyl)-

HRID 250742Notes

Reaction equation

HRID 250742 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]([NH:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])[CH:12]([CH3:14])[CH3:13].[N:26]#[C:27]Br>O1CCCC1>[C:27]([N:15]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24])#[N:26]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 2733832Lithium HexamethyldisilazideHCID 43686020HCID 43686020, compound

Product 1

HCID 86067145Cyanamide, (5-chloro-2-nitrophenyl)(2-methylpropyl)-Yield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium bis(trimethylsilyl)amide (45 mL, 1M in tetrahydrofuran) to a solution of N-[isobutyl]2-nitro-5-chloroaniline (5.2 g, 0.0226 mol) in tetrahydrofuran (50 mL) cooled in an ice bathe Stir for 30 minutes and add cyanogen bromide (5.3 g, 0.050 mol). Stir at room temperature for 3 hours. Concentrate under reduced pressure. Dissolve residue in dichloromethane, wash saturated aqueous sodium chloride, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Subject residue to silica gel chromatography, eluting with hexane/ethyl acetate mixtures to provide 5.26 g (0.021 mol) of desired compound.

Workup

  1. stirringStir at room temperature for 3 hours
  2. concentrationConcentrate under reduced pressure
  3. washDissolve residue in dichloromethane, wash saturated aqueous sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washSubject residue to silica gel chromatography, eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-30e0517fc2ae40c9b7ce1ff1d10695a7
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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