N-methyl-2-pyrrolidone → 2,2'-(Disulphanediyldiethane-2,1-diyl)bis(6-chloro-1H-benzo[de]-isoquinoline-1,3(2H)-dione)

HRID 420413Notes

Reaction equation

HRID 420413 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])O[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[ClH:17].[NH2:18][CH2:19][CH2:20][S:21][S:22][CH2:23][CH2:24][NH2:25].C(N([CH:32]([CH3:34])[CH3:33])CC)(C)C.CN1[CH2:40][CH2:39][CH2:38][C:37]1=[O:41]>>[S:21]([CH2:20][CH2:19][N:18]1[C:6](=[O:16])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[C:13]3[C:14]=2[C:9](=[CH:10][CH:11]=[CH:12]3)[C:8]1=[O:15])[S:22][CH2:23][CH2:24][N:25]1[C:8](=[O:15])[C:9]2[CH:34]=[CH:32][C:33]([Cl:17])=[C:11]3[C:10]=2[C:38](=[CH:39][CH:40]=[CH:12]3)[C:37]1=[O:41]

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidone2×HCID 776721H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-HCID 81531DiisopropylethylamineHCID 1676282-[(2-Aminoethyl)disulfanyl]ethan-1-amine hydrochloride

Product 1

HCID 594288842,2'-(Disulphanediyldiethane-2,1-diyl)bis(6-chloro-1H-benzo[de]-isoquinoline-1,3(2H)-dione)

Conditions

Temperature
120 °C

Procedure

9.30 g of 6-chloro-1H,3H-benzo[de]isochromene-1,3-dione and 4.46 g of cystamine hydrochloride were suspended in 50 ml of N-methylpyrrolidone (NMP). 5.5 g of diisopropylethylamine were added and the mixture was heated, with stirring, at 120° C. After 2 hours, 50 ml of NMP were added and the mixture continued to be stirred at 120° C. for 3 h. After cooling, the precipitated product was recovered, the filtered solution was extended by addition of 200 ml of water and a second precipitate was recovered. The precipitates were washed in water and dried. 11.46 g of white powder were recovered. The analyses showed that the product conformed to the expected structure.

Workup

  1. temperaturethe mixture was heated
  2. stirringto be stirred at 120° C. for 3 h
  3. temperatureAfter cooling
  4. customthe precipitated product was recovered
  5. additionthe filtered solution was extended by addition of 200 ml of water
  6. customa second precipitate was recovered
  7. washThe precipitates were washed in water
  8. customdried
  9. custom11.46 g of white powder were recovered

Sources & evidence

ORD record
ord-f6f5ad1e15a44681ace5f287b6ac5fdf
Source dataset
uspto-grants-2012_01
Patent number
US08097044B2

Reaction notes

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