3-Methoxyaniline → HCID 22969392, compound

HRID 2297932Notes

Reaction equation

HRID 2297932 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.[CH:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](OC2C=CC=CC=2)=[N:18][C:19]#[N:20])=[CH:12][CH:11]=1>C(#N)C>[C:19]([NH:18][C:17](=[N:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[O:16][C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)#[N:20]

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 22969392HCID 22969392, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

m-Anisidine (4.56 mL, 4.06 mmol, 1 eq.), and diphenylcyanocarbonimidate (967 mg, 4.06 mmol, 1 eq.) were mixed and refluxed in acetonitrile under N2 for 1 hour. Solids precipitated. The reaction was worked up by filtering off the solids. Obtained 580 mg as product. M.P.=170.0-171.0° C. NMR (300 MHz, DMSO-d6) δ8.70-8.50 (m, 1H); 7.43 (t, 2H, J=7 Hz); 7.40-7.20 (m, 2H); 7.14 (d, 2H, J=7 Hz); 7.00-6.80 (m, 2H); 6.80-6.70 (m, 1H); 3.80 (s, 3H).

Workup

  1. customSolids precipitated
  2. filtrationby filtering off the solids
  3. customObtained 580 mg as product

Sources & evidence

ORD record
ord-525615c22c424696905ed7d5829e6fde
Source dataset
uspto-grants-2002_12
Patent number
US06492400B1

Reaction notes

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