Acetonitrile → 5-Acenaphthyl cyanamide

HRID 898412Notes

Reaction equation

HRID 898412 reaction equation
[NH2:1][C:2]1[C:12]2[C:13]3[C:5]([CH2:6][CH2:7][C:8]=3[CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.[N:14]#[C:15]Br.C(#N)C>CCOCC.C(OCC)(=O)C>[CH2:7]1[C:8]2=[C:13]3[C:12](=[CH:11][CH:10]=[CH:9]2)[C:2]([NH:1][C:15]#[N:14])=[CH:3][CH:4]=[C:5]3[CH2:6]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 10476Cyanogen BromideHCID 625475-Aminoacenaphthene

Product 1

HCID 152843795-Acenaphthyl cyanamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-aminoacenaphthene (7.0 g, 41.4 mmol) was dissolved in a mixture of ether (100 mL) and ethyl acetate (25 mL). To this solution was added 5.2 mL of a 5 M solution of cyanogen bromide in acetonitrile (25.6 mmol of cyanogen bromide). The solution was stirred overnight, with the gradual appearance of gray precipitate. The solid was removed by filtration (the hydrobromide of 5-aminoacenaphthene) and the resulting filtrate concentrated in vacuo to afford a semi-solid residue. Ether (60 mL) was added to the residue and the mixture was stirred overnight. The solid was removed (more hydrobromide of 5-aminoacenaphthene) and the filtrate concentrate to approximately 20 mL and then diluted with warm cyclohexane (15 mL). Upon standing at room temperature, off-white crystals were deposited. They were collected, washed with cyclohexane-ether (1:1) and dried in vacuo to give 1.5 g of pure product, mp: 163-65° C.

Workup

  1. customThe solid was removed by filtration (the hydrobromide of 5-aminoacenaphthene) and the resulting filtrate
  2. concentrationconcentrated in vacuo
  3. customto afford a semi-solid residue
  4. stirringthe mixture was stirred overnight
  5. customThe solid was removed (more hydrobromide of 5-aminoacenaphthene) and the filtrate
  6. concentrationconcentrate to approximately 20 mL
  7. additiondiluted with warm cyclohexane (15 mL)
  8. customUpon standing at room temperature
  9. customThey were collected
  10. washwashed with cyclohexane-ether (1:1)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-619dbebb388149af9f86bb65a7d1156d
Source dataset
uspto-grants-2008_04
Patent number
US07351743B1

Reaction notes

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