3-(Phenylmethyl)-2-thioxo-4-thiazolidinone → 3-Benzyl-5-(3-ethylbenzothiazolylidene)rhodanine

HRID 223757Notes

Reaction equation

HRID 223757 reaction equation
C(S[C:4]1[S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[N+:8]=1[CH2:9][CH3:10])C.[CH2:15]([N:22]1[C:26](=[O:27])[CH2:25][S:24][C:23]1=[S:28])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(N(CC)CC)C>[CH2:15]([N:22]1[C:26](=[O:27])[C:25](=[S:5]2[C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[N:8]([CH2:9][CH3:10])[CH2:4]2)[S:24][C:23]1=[S:28])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 976733-(Phenylmethyl)-2-thioxo-4-thiazolidinoneHCID 1703962-Ethylmercapto-3-ethylbenzothiazolium

Product 1

HCID 867386123-Benzyl-5-(3-ethylbenzothiazolylidene)rhodanine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 30 ml of an ethanol solution of 13.0 g of the intermediate product obtained in Preparative Example 2, viz., 2-ethylmercapto-3-ethylbenzothiazolium p-toluenesulfoante, was added 4.5 g of 3-benzylrhodanine, while stirring the mixture at room temperature (about 20° C.), 6.1 g of triethylamine was added dropwise to the mixture over a 3 minute period, and thereafter, the resultant mixture was refluxed for 10 minutes. After cooling the reaction mixture, precipitate formed was recovered by filtration and recrystallized from a mixture of chloroform and ethanol to provide 4.6 g of 3-benzyl-5-(3-ethylbenzothiazolylidene)rhodanine (melting point 209° to 211° C.).

Workup

  1. additionwas added dropwise to the mixture over a 3 minute period
  2. temperatureAfter cooling the reaction mixture, precipitate
  3. customformed
  4. filtrationwas recovered by filtration
  5. customrecrystallized from a mixture of chloroform and ethanol

Sources & evidence

ORD record
ord-0520e0008641406897ad4aef1d831a68
Source dataset
uspto-grants-1982_10
Patent number
US04356247

Reaction notes

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