Triethylamine → 2-(2-Thiazolinylthio)hydrocinnamic acid ethyl ester

HRID 478043Notes

Reaction equation

HRID 478043 reaction equation
C(N(CC)CC)C.[SH:8][C:9]1[S:10][CH2:11][CH2:12][N:13]=1.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Br)[CH3:15]>C1COCC1>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:8][C:9]1[S:10][CH2:11][CH2:12][N:13]=1)[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10611137Ethyl 3-(2-bromophenyl)propanoateHCID 178527880HCID 178527880, compound

Product 1

HCID 572061812-(2-Thiazolinylthio)hydrocinnamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.4 ml of triethylamine are added dropwise to a solution of 1.8 g of 2-mercapto-1,3-thiazoline and 2.6 g of 2-bromo-hydrocinnamic acid ethyl ester in 15 ml of THF and the whole is stirred under reflux for 6 hours. The reaction mixture is filtered, the filtrate is concentrated by evaporation and the residue is partitioned between ethyl acetate and water. The organic phase is washed with water, dried, concentrated by evaporation and purified by chromatography on silica gel with eluant R. Rf (W)=0.67.

Workup

  1. temperatureunder reflux for 6 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated by evaporation
  4. customthe residue is partitioned between ethyl acetate and water
  5. washThe organic phase is washed with water
  6. customdried
  7. concentrationconcentrated by evaporation
  8. custompurified by chromatography on silica gel with eluant R

Sources & evidence

ORD record
ord-a91dde695f9748e3ab37a5f702ead165
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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