2,6-Dichlorobenzaldehyde → HCID 66967004, compound

HRID 1360717Notes

Reaction equation

HRID 1360717 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[NH2:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[NH2:20])[C:15]#[N:16]>CS(C)=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]1[NH:11][C:12]2[CH:13]=[C:14]([C:15]#[N:16])[CH:17]=[CH:18][C:19]=2[N:20]=1

Participants

4

Reactant 2

HCID 67372,6-DichlorobenzaldehydeHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 66967004HCID 66967004, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 20 ml scint. vial was added 0.500 g (2.86 mmol) of 2,6-Dichloro-benzaldehyde, 0.3804 g (2.86 mmol) of 3,4-diamino-benzonitrile, and 6 mL DMSO. To the brown solution was added 0.1995 g (1.23 mmol) of FeCl3. Allowed stir at r.t. open to air for 18 h. Extracted with EtOAc and washed with water, and brine. Dried and purified on silica gel column chromatography (EtOAc/Hep, 1:9 to 7:3) to give of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.62-7.72 (m, 4H) 7.79 (br. s., 1H) 8.27 (br. s., 1H) 13.48 (br. s., 1H). MS (m/z) 288.1 M (+1), tR=1.18, Meth 10

Workup

  1. extractionExtracted with EtOAc
  2. washwashed with water, and brine
  3. customDried
  4. custompurified on silica gel column chromatography (EtOAc/Hep, 1:9 to 7:3)

Sources & evidence

ORD record
ord-bbc9e1ee0a2a4e07a6760ff1f821226f
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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