Benzyl Bromide → HCID 9944824, compound

HRID 2183436Notes

Reaction equation

HRID 2183436 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][S:11][C:10]2=[NH:14])=[CH:4][CH:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:15]([N:14]=[C:10]1[N:9]([CH2:8][C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:13][CH2:12][S:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 98593863-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinimine

Product 1

HCID 9944824HCID 9944824, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Then, a mixture of 228 mg (1 mmol) of 3-(6-chloro-3-pyridyl)methyl-2-iminothiazolidine, 180 mg (1.05 mmol) of benzylbromide and 276 mg (2 mmol) of anhydrous potassium carbonate in 10 ml of acetonitrile was heated for 3 hours at 90° C. under refluxing. After the reaction mixture was cooled to the room temperature, the solvent was removed under reduced pressure. The resulting residue was mixed with dichloromethane and saturated sodium hydrogen carbonate aqueous solution, and the organic layer was separated. The water layer was extracted with dichloromethane, and combined organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; hexane:ethyl acetate=2:1) to give 217 mg (yield; 68.3%) of 2-benzylimino-3-(6-chloro-3-pyridyl)methylthiazolidine as colorless oil. This product was dissolved in methanol and to this solution was added 79 mg (0.681 mmol) of fumaric acid, and the mixture was concentrated under reduced pressure. The resulting residue was treated with acetonitrile to give crystalline. The crystalline was collected by filtration and dried in vacuum to give 271 mg of fumarate of the title Compound 14.

Workup

  1. temperatureunder refluxing
  2. temperatureAfter the reaction mixture was cooled to the room temperature
  3. customthe solvent was removed under reduced pressure
  4. additionThe resulting residue was mixed with dichloromethane and saturated sodium hydrogen carbonate aqueous solution
  5. customthe organic layer was separated
  6. extractionThe water layer was extracted with dichloromethane
  7. dry with materialwas dried over magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe resulting residue was purified by aminopropyl-coated silica gel (Chromatorex NH-type; Fuji Silysia Chemical Ltd.) column chromatography (eluent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4c4d4466e6bd48ddb13105ef30a89546
Source dataset
uspto-grants-2005_05
Patent number
US06900202B2

Reaction notes

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