N-methyl-2-pyrrolidone → HCID 86609787, compound

HRID 2241799Notes

Reaction equation

HRID 2241799 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:32]=[CH:31][C:25](/[CH:26]=[CH:27]/[C:28](Cl)=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20].CN1[C:38](=[O:39])CCC1>>[NH2:18][C:7]1[C:6]([S:5][CH2:4][CH2:3][C:1]#[N:2])=[CH:11][C:10]([N:12]([C:28](=[O:29])/[CH:27]=[CH:26]/[C:25]2[CH:31]=[CH:32][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=2)[CH:38]=[O:39])=[C:9]([S:13][CH2:14][CH2:15][C:16]#[N:17])[CH:8]=1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 5971362trans-4-Nitrocinnamoyl chlorideHCID 685424943,3'-[(2,5-Diamino-1,4-phenylene)disulfanediyl]dipropanenitrile

Product 1

HCID 86609787HCID 86609787, compoundYield 78.13%

Conditions

Temperature
0 °C

Procedure

2,5-Bis[(cyanoethyl)thio]-1,4-phenylenediamine (2.50 g, 9.00 mmol) was admixed with 15 mL of NMP in a 250 mL 3-necked round-bottom flask with nitrogen purge. The resultant mixture was cooled to around 0° C. in an ice bath with stirring, followed by the addition of trans-4-nitrocinnamoyl chloride (2.00 g, 9.45 mmol, dissolved in 13 mL NMP) drop by drop. Thereafter, the ice bath was removed, and 400 mL of water was poured into the flask to result in the formation of a solid precipitate, which was collected by filtration. The thus-obtained solid was added into 400 mL of water and heated to 60° C. for 10 min. After filtration, the collected solid was admixed with 600 mL of methanol, followed by filtration. An orange solid was obtained and dried in a vacuum oven at 80° C., giving the title compound in a yield of 78.13%.

Workup

  1. custompurge
  2. customThereafter, the ice bath was removed
  3. addition400 mL of water was poured into the flask
  4. customto result in the formation of a solid precipitate, which
  5. filtrationwas collected by filtration
  6. additionThe thus-obtained solid was added into 400 mL of water
  7. temperatureheated to 60° C. for 10 min
  8. filtrationAfter filtration
  9. filtrationfollowed by filtration
  10. customAn orange solid was obtained
  11. customdried in a vacuum oven at 80° C.

Sources & evidence

ORD record
ord-86eb825809584f478892c46a02d97ed1
Source dataset
uspto-grants-2010_03
Patent number
US07670512B2

Reaction notes

Loading…