4,5-Dihydro-2-thiazolamine → 3-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinimine

HRID 2183435Notes

Reaction equation

HRID 2183435 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.Br[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[N:13][CH:14]=1>C(#N)C>[Cl:15][C:12]1[N:13]=[CH:14][C:9]([CH2:8][N:6]2[CH2:5][CH2:4][S:3][C:2]2=[NH:1])=[CH:10][CH:11]=1.[Cl:15][C:12]1[N:13]=[CH:14][C:9]([CH2:8][N:6]2[CH2:5][CH2:4][S:3][C:2]2=[N:1][CH2:8][C:9]2[CH:14]=[N:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 64246615-(Bromomethyl)-2-chloropyridine

Product 2

HCID 98593863-[(6-Chloro-3-pyridinyl)methyl]-2-thiazolidinimineYield 54.7%HCID 9946544HCID 9946544, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 511 mg (5 mmol) of 2-amino-2-thiazoline and 1.03 g (5 mmol) of 5-bromomethyl-2-chloropyridine in 50 ml of acetonitrile was heated for 6 hours at 90° C. under refluxing. Then, the reaction mixture was cooled to the room temperature, and 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 623 mg (yield; 54.7%) of 3-(6-chloro-3-pyridyl)methyl-2-iminothiazolidine as yellow oil and 173 mg (yield; 7.4%) of 3-(6-chloro-3-pyridyl)methyl-2-[(6-chloro-3-pyridyl)methyl]iminothiazolidine as yellow oil.

Workup

  1. temperatureunder refluxing
  2. temperatureThen, 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-931482c65c0046b595c6e49a35bb303d
Source dataset
uspto-grants-2005_05
Patent number
US06900202B2

Reaction notes

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