Aniline → Phenylcyanamide

HRID 570289Notes

Reaction equation

HRID 570289 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 mmo) 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-bd3b68a5c3924737a37b4b04fbbdb95a
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

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