Dimethylacetamide → HCID 178483475, compound

HRID 2236792Notes

Reaction equation

HRID 2236792 reaction equation
C(Cl)(=O)C(Cl)=[O:3].C([O:10][C:11]1[CH:16]=[C:15]([CH2:17][NH:18]/[CH:19]=[C:20]2\[C:21](=[O:32])[NH:22][C:23](=[O:31])[C:24]3[C:29]\2=[CH:28][C:27]([I:30])=[CH:26][CH:25]=3)[CH:14]=[CH:13][C:12]=1[NH:33][C:34](=[O:36])[CH3:35])(=O)C.[CH3:37][N:38]([CH3:42])[C:39](=O)[CH3:40]>ClCCl>[OH-:3].[NH4+:18].[CH3:37][N:38]([CH3:42])[CH2:39]/[CH:40]=[CH:35]/[C:34]([NH:33][C:12]1[CH:13]=[CH:14][C:15]([CH2:17][NH:18]/[CH:19]=[C:20]2\[C:21](=[O:32])[NH:22][C:23](=[O:31])[C:24]3[C:29]\2=[CH:28][C:27]([I:30])=[CH:26][CH:25]=3)=[CH:16][C:11]=1[OH:10])=[O:36]

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 65578Oxalyl chlorideHCID 178474198HCID 178474198, compound

Product 2

HCID 14923Ammonium HydroxideYield 1.5%HCID 178483475HCID 178483475, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

An amount of 8.3 g (50.6 mmol) of (E)-4-(dimethylamino)-2-butenioc acid is added excess of 2.0M oxalyl chloride (10 mL) and refluxed at 60° C. until all the solid is in solution. To a separate flask is added 2.2 g (5.06 mmol) of ′2-(acetylamino)-5-({[(Z)-(6-iodo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)phenyl acetate, and N,N-dimethylacetamide (5 mL) and placed in an ice bath for ten minutes. The mixture containing the acid chloride is cooled to room temperature and evaporated to dryness. Dichloromethane (5 mL) is added and transferred to the flask in the ice bath slowly. The mixture is allowed to stir in the ice bath for 3 hours. It is evaporated and purified by column chromatography with 10% methanol: 80% dichloromethane: 1.5% ammonium hydroxide to give the desired product (1.2 g 43% yield) as a light-brown solid.; mp 185-186° C.

Workup

  1. waitplaced in an ice bath for ten minutes
  2. temperatureis cooled to room temperature
  3. customevaporated to dryness
  4. additionDichloromethane (5 mL) is added
  5. customIt is evaporated
  6. custompurified by column chromatography with 10% methanol

Sources & evidence

ORD record
ord-698d9df599bf40c3b014ca6588079f0b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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