Toluene → HCID 14051170, compound

HRID 1199703Notes

Reaction equation

HRID 1199703 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)/[CH:12]=[CH:13]/[C:14]1[S:15][CH:16]=[C:17]([CH2:19][CH2:20][CH3:21])[N:18]=1.Br[CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30].[OH-].[Na+]>C(O)C.C(N(CC)CC)C>[C:29]([CH2:28][CH2:27][CH2:26][NH:8][C:9]1[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=1)/[CH:12]=[CH:13]/[C:14]1[S:15][CH:16]=[C:17]([CH2:19][CH2:20][CH3:21])[N:18]=1)([OH:31])=[O:30]

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrateHCID 14051194HCID 14051194, compound

Product 1

HCID 14051170HCID 14051170, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 20 ml of toluene were added 732 mg of 2-(trans-3-aminostyryl)-4-propylthiazole, 1170 mg of ethyl 4-bromobutyrate and 606 mg of triethylamine, and the reaction was carried out at 100° C. for 21 hours. After the reaction mixture was cooled to room temperature, 10 ml of ethanol and 10 ml of an aqueous 5% sodium hydroxide solution were added and the mixture was stirred at room temperature for 1.5 hours to effect hydrolysis of the ester. After completion of the reaction, ethanol was evaporated under reduced pressure and the residue was adjusted to pH 1-2 with addition of 10% hydrochloric acid, followed by extraction with ethyl ether. After drying over anhydrous magnesium sulfate, the solvent was evaporated and the solid formed was recrystallized from ethyl ether to give 629 mg (yield 64%) of the title compound.

Workup

  1. customwas evaporated under reduced pressure
  2. additionthe residue was adjusted to pH 1-2 with addition of 10% hydrochloric acid
  3. extractionfollowed by extraction with ethyl ether
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customthe solid formed
  7. customwas recrystallized from ethyl ether

Sources & evidence

ORD record
ord-2652e03d6d1440779a7bc9a227dfd145
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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