Thiophenol → HCID 14328153, compound

HRID 330069Notes

Reaction equation

HRID 330069 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH2:16][NH:17][C:18](=[O:30])[CH2:19][O:20][C:21]1[C:26]([CH3:27])=[N:25][C:24]([CH3:28])=[C:23]([CH3:29])[N:22]=1>CN(C)C=O>[C:1]1([S:7][CH2:15][CH2:16][NH:17][C:18](=[O:30])[CH2:19][O:20][C:21]2[C:26]([CH3:27])=[N:25][C:24]([CH3:28])=[C:23]([CH3:29])[N:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 14328128HCID 14328128, compound

Product 1

HCID 14328153HCID 14328153, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thiophenol (0.60 g, 5.4 mM) and potassium carbonate (0.75 g, 5.4 mM) were added to compound 648 (0.91 g, 3.0 mM) dissolved in dimethylformamide (10 ml) and the mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo, the residue was dissolved in chloroform and washed with dilute aqueous potassium carbonate. The aqueous layer was further extracted with chloroform. The combined organic layer was chromatographed by eluting successively with benzene and benzene-ethyl acetate (10:1) to obtain the product (0.35 g, yield: 35.2%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with dilute aqueous potassium carbonate
  4. extractionThe aqueous layer was further extracted with chloroform
  5. customThe combined organic layer was chromatographed
  6. washby eluting successively with benzene and benzene-ethyl acetate (10:1)

Sources & evidence

ORD record
ord-fead24d155f84dd7b08c6f8ed5ce7a41
Source dataset
uspto-grants-1990_01
Patent number
US04894453

Reaction notes

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