Aniline → Phenylcyanamide

HRID 405772Notes

Reaction equation

HRID 405772 reaction equation
Br[C:2]#[N:3].CC([O-])=O.[K+].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO>[C:10]1([NH:9][C:2]#[N:3])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 10476Cyanogen BromideHCID 517044Potassium Acetate

Product 1

HCID 69318Phenylcyanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of BrCN (0.11 g, 1.1 mmol) in MeOH (10 mL) at 0° C. was added solid KOAc (0.32 g, 3.3 mmol) and a solution of aniline (0.1 mL, 1.1 mmol) in MeOH (1 mL). The reaction was stirred for 3 hours then partitioned with water (15 mL) and dichloromethane (25 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered and reduced to dryness to afford N-phenylcyanamide, which was immediately used without purification.

Workup

  1. customthen partitioned with water (15 mL) and dichloromethane (25 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-63a6eeebb60242dc81153c9afdc9727c
Source dataset
uspto-grants-2014_06
Patent number
US08754071B2

Reaction notes

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