Water → HCID 68539998, compound

HRID 2241798Notes

Reaction equation

HRID 2241798 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×

Conditions

Temperature
2.5 °C

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

Sources & evidence

ORD record
ord-bedca31e5450412c9646e964a46366ba
Source dataset
uspto-grants-2010_03
Patent number
US07670512B2

Reaction notes

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