Hydrogen Bromide → HCID 59264693, compound

HRID 646406Notes

Reaction equation

HRID 646406 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[S:13])[NH2:12])=[CH:7][CH:6]=1)[CH3:2].Br[CH2:16][C:17]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=O.Br>C(O)(C)C.C(OCC)C>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:13][CH:16]=[C:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 1514083-(2-Bromoacetyl)pyridineHCID 54189111Ethyl 4-(aminothioxomethyl)benzoate

Product 1

HCID 59264693HCID 59264693, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

4-Thiocarbamoyl-benzoic acid ethyl ester (CAS 78950-31-9) (0.4 g, 1.91 mmol), and 2-Bromo-1-pyridin-3-yl-ethanone; hydrobromide (CAS 17694-68-7) (0.537 g, 1.91 mmol) is placed in a 100 mL flask and dissolved in 20 mL of isopropyl alcohol. The mixture is heated to reflux for 1.5 hours and cooled and diluted with 40 mL of diethyl ether. The resulting solid is filtered and dissolved in a mixture of dichloromethane and saturated sodium bicarbonate solution. The organics are separated, dried over sodium sulfate, filtered and concentrated to provide 0.565 g of the titled compound. MS (m/e) 311.1 (M+1)

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturecooled
  4. filtrationThe resulting solid is filtered
  5. dissolutiondissolved in a mixture of dichloromethane and saturated sodium bicarbonate solution
  6. customThe organics are separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8b743cc858d344dfb2b1f7946183dce0
Source dataset
uspto-grants-2010_04
Patent number
US07705025B2

Reaction notes

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