Aniline → HCID 19813282, compound

HRID 466983Notes

Reaction equation

HRID 466983 reaction equation
[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]([C:13]([O:15]C(OCC)=O)=O)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[S:3]1[CH:4]=[CH:5][S:1][C:2]1=[C:6]([C:13](=[O:15])[NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:7]([O:9][CH:10]([CH3:11])[CH3:12])=[O:8]

Participants

4

Reactant 2

HCID 6115AnilineHCID 19813261HCID 19813261, compound

Product 1

HCID 19813282HCID 19813282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isopropyl 2-(1,3-dithiol-2-ylidene)-2-(ethoxycarbonyloxy-carbonyl)acetate (12.72 g) and aniline (3.73 g) were dissolved in methylene chloride (100 ml). The mixture was stirred at room temperature for 24 hrs. The reaction mixture was washed with aqueous sodium hydroxide solution, dil-HCl and then water. The methylene chloride layer was dried and the solvent was distilled. The resultant residue was recrystallized from ethyl acetate to obtain the pure product. (11.3 g, 88.0%)

Workup

  1. washThe reaction mixture was washed with aqueous sodium hydroxide solution
  2. dry with materialThe methylene chloride layer was dried
  3. distillationthe solvent was distilled
  4. customThe resultant residue was recrystallized from ethyl acetate
  5. customto obtain the pure product

Sources & evidence

ORD record
ord-f1b73f64f1a44e5f932bdb4c10e96784
Source dataset
uspto-grants-1992_10
Patent number
US05158950

Reaction notes

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