Ethyl Acetate → HCID 9946949, compound

HRID 1743153Notes

Reaction equation

HRID 1743153 reaction equation
C(O[C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18])C.[Cl:21][C:22]1[C:28](Cl)=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24].C(OC(=O)C)C>CS(C)=O>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH:24][C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 118442,3-DichloroanilineHCID 222385043-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione

Product 1

HCID 9946949HCID 9946949, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione (0.40 g, 1.44 mmol) and 2,3-dichloroaniline (0.34 g, 2.10 mmol) in 2 mL DMSO was heated at 110° C. for overnight. The reaction mixture was cooled to room temperature, and ethylacetate was added, a precipitate formed. The filter cake was collected. Titration from acetone and hexanes gave 68 mg (11%) of 3-(2-chloroanilino)-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione. LCMS(H+) 394.

Workup

  1. customa precipitate formed
  2. customThe filter cake was collected

Sources & evidence

ORD record
ord-c59926fda354401f9c8662dde0dc7765
Source dataset
uspto-grants-2006_03
Patent number
US07008962B2

Reaction notes

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