Acetic Anhydride → 6-((4-(4-cyano-5-(dicyanomethylene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexyl acetate

HRID 607492Notes

Reaction equation

HRID 607492 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[Na].[Na].[C:35]([C:37]1[C:41](=[C:42]([C:45]#[N:46])[C:43]#[N:44])[NH:40][C:39](=[O:47])[C:38]=1O)#[N:36].O=P(Cl)(Cl)Cl>CN(C)C=O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]([C:12]1[CH:13]=[CH:14][C:15]([C:38]2[C:39](=[O:47])[NH:40][C:41](=[C:42]([C:45]#[N:46])[C:43]#[N:44])[C:37]=2[C:35]#[N:36])=[CH:16][CH:17]=1)[CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 24813Phosphorus oxychlorideHCID 578577296-((2-Ethylhexyl)(phenyl)amino)hexyl acetateHCID 866340934-Cyano-5-dicyanomethylene-3-hydroxy-2-oxo-3-pyrroline disodium salt

Product 1

HCID 866340946-((4-(4-cyano-5-(dicyanomethylene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexyl acetateYield 38.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a three-neck flask, 6-((2-ethylhexyl)(phenyl)amino)hexyl acetate (7.0 g, 0.020 mol) was dissolved in dimethylformamide (100 ml), stirred, and added with acetic anhydride (2.9 g, 0.028 mol) and 4-cyano-5-dicyanomethylene-3-hydroxy-2-oxo-3-pyrroline disodium salt (5.6 g, 0.024 mol). The temperature was decreased to 0° C., after which POCl3 was slowly added thereto for 30 min, and the mixture was allowed to react at room temperature for 6 hours with stirring. A solid product was precipitated with water, filtered, and then dried, thus obtaining 4.0 g of a dark blue solid.

Workup

  1. customwas decreased to 0° C.
  2. customto react at room temperature for 6 hours
  3. stirringwith stirring
  4. customA solid product was precipitated with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-70b8be560a674c16b274ff5c91c2b4c3
Source dataset
uspto-grants-2011_03
Patent number
US07915428B2

Reaction notes

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