HCID 13186366, compound → HCID 135816716, compound

HRID 1388301Notes

Reaction equation

HRID 1388301 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([CH2:14][S:15]([NH:18][C:19](=[O:25])[C:20](OCC)=[O:21])(=[O:17])=[O:16])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C)([O-])C.[K+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([C:14]3[S:15](=[O:17])(=[O:16])[NH:18][C:19](=[O:25])[C:20]=3[OH:21])[S:12][CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 13186366HCID 13186366, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 135816716HCID 135816716, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the 2-thiazolylmethyl substituted oxamate intermediate prepared in Step B above (1.0 g., 0.0024 mol) in dimethylformamide (5 ml) was added potassium tert-butoxide (0.55 g, 0.0048 ml) in several portions over 15 minutes. The mixture was stirred at room temperature for 24 hours. After diluting with water (30 ml) and acidifying to congo red indicator paper, a yellow gum (1.1 g.) was obtained. Recrystallization was achieved by dissolving in boiling ether (500 ml), filtering, concentrating to a small volume, and adding petroleum ether. The yield of the title product was 0.3 g., m.p. 250° C. (dec.).

Workup

  1. customa yellow gum (1.1 g.) was obtained
  2. customRecrystallization
  3. dissolutionby dissolving
  4. filtrationfiltering
  5. concentrationconcentrating to a small volume
  6. additionadding petroleum ether

Sources & evidence

ORD record
ord-324758f573fe45e89ad51a03f20c6c08
Source dataset
uspto-grants-1984_02
Patent number
US04431652

Reaction notes

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