Hantzsch ester → HCID 73455757, compound

HRID 1058641Notes

Reaction equation

HRID 1058641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][S:6][C:7]1[NH:12][C:11](=O)[CH:10]=[C:9]([CH:14]=[C:15]2[S:19][C:18](=[S:20])[NH:17][C:16]2=[O:21])[N:8]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][S:6][C:7]1[N:8]=[C:9]([CH:14]=[C:15]2[S:19][C:18](=[S:20])[NH:17][C:16]2=[O:21])[CH:10]=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 70849Hantzsch esterHCID 136388325HCID 136388325, compound

Product 1

HCID 73455757HCID 73455757, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 5-(2-(3,4-dichlorobenzylthio)pyrimidin-4-ylmethylidene)rhodanine (Example 25, 0.3 mmol) in toluene (5 mL) was added diethyl 2,6-dimethyl-1,4-dihydro-3,5-pyridine dicarboxylate (109 mg, 0.39 mmol) and 0.3 g of activated silica gel. The mixture was heated to 80° C. for 20 h then filtered while warm. The filter cake was rinsed with ethyl acetate and the combined filtrates were evaporated to dryness. The residue was redissolved in ethyl acetate and extracted with 1 N aqueous hydrochloric acid. The organic layer was dried (sodium sulfate) and concentrated to give 11 mg of pure product.

Workup

  1. filtrationthen filtered
  2. temperaturewhile warm
  3. washThe filter cake was rinsed with ethyl acetate
  4. customthe combined filtrates were evaporated to dryness
  5. dissolutionThe residue was redissolved in ethyl acetate
  6. extractionextracted with 1 N aqueous hydrochloric acid
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0829ba0b273b4464b2ee8f317d538e26
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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