Water → HCID 68539998, compound

HRID 2242411Notes

Reaction equation

HRID 2242411 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[NH2:18])#[N:2].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].O>CN1C(=O)CCC1>[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:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 85024-Nitrobenzoyl chlorideHCID 685424943,3'-[(2,5-Diamino-1,4-phenylene)disulfanediyl]dipropanenitrile

Product 1

HCID 68539998HCID 68539998, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

2,5-Bis[(cyanoethyl)thio]-1,4-phenylenediamine (13.9 g, 50 mmol) was dissolved in 90 mL of NMP in a 250 mL 3-necked round-bottom flask under nitrogen purge. The resultant clear red solution was cooled to 0˜5° C. in an ice bath, followed by addition of freshly distilled triethylamine (TEA) by syringe. After stirring for 10 minutes, a mixture of 4-nitrobenzoyl chloride (10.2 g, 55 mmol) and 90 mL of NMP was added into the stirred red solution drop by drop over a period of 0.5 h. The resultant solution was stirred at 0˜5° C. for 2 h and at room temperature for 1 h, followed by addition of 800 mL of water with stirring. The resultant yellow precipitate was collected by filtration, followed by washing with 800 mL of deionized water twice and 300 mL of methanol once. The obtained product was extracted with methanol using a Soxhlet extractor for 24 h. A yellow solution was collected and evaporated, followed by drying at 60° C. under vacuum overnight, giving the title compound as a red powder (13.1 g, yield 61%).

Workup

  1. custompurge
  2. temperatureThe resultant clear red solution was cooled to 0˜5° C. in an ice bath
  3. additionfollowed by addition of freshly distilled triethylamine (TEA) by syringe
  4. additionwas added into the stirred red solution drop by drop over a period of 0.5 h
  5. stirringwith stirring
  6. filtrationThe resultant yellow precipitate was collected by filtration
  7. washby washing with 800 mL of deionized water twice
  8. extractionThe obtained product was extracted with methanol using a Soxhlet extractor for 24 h
  9. customA yellow solution was collected
  10. customevaporated
  11. customby drying at 60° C. under vacuum overnight

Sources & evidence

ORD record
ord-01d3fa31217946f9a069eafc32c887bc
Source dataset
uspto-grants-2010_03
Patent number
US07671141B2

Reaction notes

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