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

HRID 607494Notes

Reaction equation

HRID 607494 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)C.C(OC(=O)C)(=[O:28])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:35]([C:37]1[C:41](=[C:42]([C:43]#[N:44])[C:45]#[N:46])[NH:40][C:39](=[O:47])[C:38]=1[C:15]1[CH:16]=[CH:17][C:12]([N:11]([CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([O:4][CH3:1])=[O:28])=[CH:13][CH:14]=1)#[N:36]

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 86634095methyl 6-((4(4-cyano-5-(dicyanomethylene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoateYield 39.9%

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 added to dimethylformamide (100 ml), stirred, and then 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., POCl3 was slowly added thereto for 30 min, and then 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-e726ca1bb224449789bf102f5315e252
Source dataset
uspto-grants-2011_03
Patent number
US07915428B2

Reaction notes

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