Reaction #2328982

Reaction equation

2,5-Bis[(2-cyanoethyl)sulfanyl]-N-(4-nitrobenzoyl)-1,4-phenylenediamine

4-hydroxybenzoic acid

→

title compound

Yield 76.3%

2,5-bis[(2-cyanoethyl)sulfanyl]-N-(p-hydroxybenzoyl)-N′-(p-nitrobenzoyl)-p-phenylenediamine

Yield 76.3%

Solvents

NMP

Conditions

Workup

1. 1
   Otherpurge
2. 2
   workup.ADDITIONfollowed by addition of lithium chloride (LiCl, 0.58 g), triphenylphosphite (TPP, 2.92 mL) and pyridine (2.92 mL)
3. 3
   TemperatureThe resultant mixture was heated to a temperature of 80˜95° C. for about 4 h
4. 4
   workup.ADDITION400 mL of water was subsequently added
5. 5
   Filtrationthe resultant precipitate was collected by filtration
6. 6
   Washwashed with water (400 mL
7. 7
   Otherby drying at room temperature under vacuum overnight

Procedure

2,5-Bis[(2-cyanoethyl)sulfanyl]-N-(4-nitrobenzoyl)-1,4-phenylenediamine (1.0 g, 2.34 mmol) as prepared from the above Example 1 was admixed with 4-hydroxybenzoic acid (0.328 g, 2.38 mmol) in 11.7 mL NMP under nitrogen purge, followed by addition of lithium chloride (LiCl, 0.58 g), triphenylphosphite (TPP, 2.92 mL) and pyridine (2.92 mL). The resultant mixture was heated to a temperature of 80˜95° C. for about 4 h, followed by cooling to room temperature. 400 mL of water was subsequently added with stirring for a few minutes, and the resultant precipitate was collected by filtration, washed with water (400 mL, twice) and methanol (400 mL, once), followed by drying at room temperature under vacuum overnight, giving the title compound in a yield of 76.3%.

Source