Toluene → HCID 14051164, compound

HRID 1199698Notes

Reaction equation

HRID 1199698 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]#[N:31]>C(N(CC)CC)C>[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)#[N:31]

Participants

5

Reactant 3

HCID 1140TolueneHCID 214124-BromobutyronitrileHCID 14051212HCID 14051212, compound

Product 1

HCID 14051164HCID 14051164, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 50 ml of toluene were added 2.02 g of triethylamine and 5.04 g of 2-(trans-3-aminostyryl)benzothiazole at room temperature, and then 2.96 g of 4-bromobutyronitrile was added to carry out the reaction at 110° C. for 7 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. After evaporation of the solvent under reduced pressure, the residue was purified through silica gel column chromatography by use of ethyl acetate-ethyl ether-n-hexane (2:5:5) to give 2.55 g (yield 40%) of the title compound as colorless oily product.

Workup

  1. customthe reaction at 110° C. for 7 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. customAfter evaporation of the solvent under reduced pressure
  5. customthe residue was purified through silica gel column chromatography by use of ethyl acetate-ethyl ether-n-hexane (2:5:5)

Sources & evidence

ORD record
ord-dc8f7a56c41f4e089a431ad15928bbac
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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