Piperidine → 5-[2-(3-Phenylureido)thiazol-4-ylmethylene]rhodanine-3-acetic acid

HRID 2107171Notes

Reaction equation

HRID 2107171 reaction equation
[C:1]1([NH:7][C:8](=[O:17])[NH:9][C:10]2[S:11][CH:12]=[C:13]([CH:15]=O)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:18]1[CH2:24][C:22](=[O:23])[N:21]([CH2:25][C:26]([OH:28])=[O:27])[C:19]1=[S:20].N1CCCCC1>C(O)C>[C:1]1([NH:7][C:8](=[O:17])[NH:9][C:10]2[S:11][CH:12]=[C:13]([CH:15]=[C:24]3[S:18][C:19](=[S:20])[N:21]([CH2:25][C:26]([OH:28])=[O:27])[C:22]3=[O:23])[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 150535142-(3-Phenylureido)thiazole-4-carbaldehyde

Product 1

HCID 544121855-[2-(3-Phenylureido)thiazol-4-ylmethylene]rhodanine-3-acetic acidYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 1 g of 2-(3-phenylureido)thiazole-4-carbaldehyde, 0.85 g of rhodanine-3-acetic acid, 0.76 g of piperidine and 15 ml of ethanol was stirred at room temperature for 2 hours, and the resulting mixture was left to stand overnight. The crystals which precipitated out were collected by filtration dispersed in dilute aqueous hydrochloric acid, and washed with stirring for 30 minutes. The resulting crystalline product was recrystallized from a mixture of acetic acid and ethyl acetate, giving 0.78 g of the desired compound as an orange powder.

Workup

  1. waitthe resulting mixture was left
  2. waitto stand overnight
  3. customThe crystals which precipitated out
  4. filtrationwere collected by filtration
  5. additiondispersed in dilute aqueous hydrochloric acid
  6. washwashed
  7. stirringwith stirring for 30 minutes
  8. customThe resulting crystalline product was recrystallized from a mixture of acetic acid and ethyl acetate

Sources & evidence

ORD record
ord-7b4ddc6af69b4c5999e9c08d89975569
Source dataset
uspto-grants-1990_06
Patent number
US04933355

Reaction notes

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