3-Rhodanineacetic acid, ethyl ester → 3-Carboethoxymethyl-5-(3-ethylbenzothiazolylidene)rhodanine

HRID 223756Notes

Reaction equation

HRID 223756 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.C(S[C:15]1[S:16][C:17]2[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[N+:19]=1[CH2:20][CH3:21])C.[C:26]([CH2:31][N:32]1[C:36](=[O:37])[CH2:35][S:34][C:33]1=[S:38])([O:28][CH2:29][CH3:30])=[O:27]>C(N(CC)CC)C>[C:26]([CH2:31][N:32]1[C:36](=[O:37])[C:35](=[S:16]2[C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[N:19]([CH2:20][CH3:21])[CH2:15]2)[S:34][C:33]1=[S:38])([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 1410093-Rhodanineacetic acid, ethyl esterHCID 140905473-Ethyl-2-(ethylsulfanyl)-1,3-benzothiazol-3-ium 4-methylbenzene-1-sulfonate

Product 1

HCID 569851713-Carboethoxymethyl-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-toluenesulfonate, was added 4.4 g of 3-carboethoxymethylrhodanine, while stirring the mixture at room temperature (about 20° C.), 6.1 g of triethylamine was added dropwise to the solution over a 3 minute period, and thereafter the resultant mixture was refluxed for 10 minutes. After cooling the reaction mixture, precipitates formed were recovered by filtration and recrystallized from a mixture of chloroform and ethanol to provide 1.1 g of 3-carboethoxymethyl-5-(3-ethylbenzothiazolylidene)rhodanine (melting point 250° to 252° C.).

Workup

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

Sources & evidence

ORD record
ord-92dec17161f442d2b2a367d90b07aabe
Source dataset
uspto-grants-1982_10
Patent number
US04356247

Reaction notes

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