Triethylamine → HCID 2727044, compound

HRID 1857474Notes

Reaction equation

HRID 1857474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[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(CC)CC)C>ClCCl>[C:19]([NH:18][C:17](=[N:5][C:4]1[CH:3]=[C:2]([Cl:1])[CH:8]=[C:7]([Cl:9])[CH:6]=1)[O:16][C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)#[N:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122813,5-DichloroanilineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 2727044HCID 2727044, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-dichloroaniline (11 mmol, 1.79 g) in dichloromethane (25 ml), diphenylcyanocarbonimidate (10 mmol, 2.38 g) and triethylamine (11 mmol, 1.53 ml) were added. The reaction mixture was stirred under nitrogen for 65 h at room temperature. After concentration the residue was stirred with water, the water was decanted followed by concentration. The residue was stirred with toluene and the solid was collected by filtration giving 2.04 g of the title compound (67%); 1H-NMR (CDCl3): δ 7.12 (d, 2H), 7.22 (s, 1H), 7,35 (m, 3H), 7.45 (d, 2H), 9.4 ppm (br s,1H). EI SP/MS: 305 (M+), 307 (M+2), 309 (M+4).

Workup

  1. concentrationAfter concentration the residue
  2. stirringwas stirred with water
  3. customthe water was decanted
  4. concentrationfollowed by concentration
  5. stirringThe residue was stirred with toluene
  6. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-22dda6cd6cc94db8a2fbbfbaf092584f
Source dataset
uspto-grants-2000_11
Patent number
US06147098

Reaction notes

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