4-Hydroxybenzoic Acid → HCID 68543655, compound

HRID 2242413Notes

Reaction equation

HRID 2242413 reaction equation
[C:1]([CH2:3][CH2:4][S:5][C:6]1[CH:11]=[C:10]([NH2:12])[C:9]([S:13][CH2:14][CH2:15][C:16]#[N:17])=[CH:8][C:7]=1[NH:18][C:19](=[O:29])[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)#[N:2].[OH:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=1>CN1C(=O)CCC1>[C:16]([CH2:15][CH2:14][S:13][C:9]1[CH:8]=[C:7]([NH:18][C:19](=[O:29])[C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[C:6]([S:5][CH2:4][CH2:3][C:1]#[N:2])=[CH:11][C:10]=1[NH:12][C:35](=[O:36])[C:34]1[CH:38]=[CH:39][C:31]([OH:30])=[CH:32][CH:33]=1)#[N:17]

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 68539998HCID 68539998, compound

Product 1

HCID 68543655HCID 68543655, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

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%.

Workup

  1. custompurge
  2. additionfollowed by addition of lithium chloride (LiCl, 0.58 g), triphenylphosphite (TPP, 2.92 mL) and pyridine (2.92 mL)
  3. temperatureThe resultant mixture was heated to a temperature of 80˜95° C. for about 4 h
  4. addition400 mL of water was subsequently added
  5. filtrationthe resultant precipitate was collected by filtration
  6. washwashed with water (400 mL
  7. customby drying at room temperature under vacuum overnight

Sources & evidence

ORD record
ord-f06f54a065fe43d3a42ee8af84d88752
Source dataset
uspto-grants-2010_03
Patent number
US07671141B2

Reaction notes

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