Toluene → HCID 14051174, compound

HRID 1199704Notes

Reaction equation

HRID 1199704 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)/[CH:12]=[CH:13]/[C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.Br[CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(N(CC)CC)C>[CH2:33]([O:32][C:30]([CH2:29][CH2:28][CH2:27][NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)/[CH:12]=[CH:13]/[C:14]1[S:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 1140TolueneHCID 76300Ethyl 4-bromobutyrateHCID 14051212HCID 14051212, compound

Product 1

HCID 14051174HCID 14051174, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

To 10 ml of toluene were added 1.0 g of 2-(trans-3-aminostyryl)benzothiazole, 0.78 g of ethyl 4-bromobutyrate and 0.4 g of triethylamine, and the mixture was stirred at 100° C. for 20 hours. After cooled to room temperature, the mixture was extracted with toluene, dried over anhydrous magnesium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography by use of ethyl acetate-n-hexane to obtain 951 mg of the title compound (yield 66%).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe mixture was extracted with toluene
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography by use of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b91b1e29b4dc4b60b2a73d470d10a690
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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