Thiazolidine → 2-Chloro-4-morpholino-6-(3-thiazolidinyl)-1,3,5-triazine

HRID 2395612Notes

Reaction equation

HRID 2395612 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[S:21]1[CH2:25][CH2:24][NH:23][CH2:22]1>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=[C:2]([N:23]2[CH2:24][CH2:25][S:21][CH2:22]2)[N:7]=1

Participants

5

Reactant 3

HCID 10444ThiazolidineHCID 11430Potassium CarbonateHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazine

Product 1

HCID 105413232-Chloro-4-morpholino-6-(3-thiazolidinyl)-1,3,5-triazineYield 29.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The obtained 2,4-dichloro-6-morpholino-1,3,5-triazine (237 mg, 1.00 mmol) was dissolved in DMF (3 ml), added with anhydrous potassium carbonate (138 mg, 1.00 mmol) and cooled to -5° C.-0° C. This mixture was gradually added dropwise with thiazolidine (103 mg, 1.15 mmol) dissolved in DMF (1 ml). The reaction mixture was stirred at room temperature overnight and was evaporated under reduced pressure. The residue was added with ethyl acetate and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water, dried over anhydrous magnesium sulfate and evaporated. The residue obtained was purified by silica gel column chromatography, using n-hexane and ethyl acetate (7:3) as eluant, to obtain 282 mg (yield: 97.2%) of 2-chloro-4-morpholino-6-(3-thiazolidinyl)-1,3,5-triazine having melting point of 137° C.-139.5° C. (3) The obtained 2-chloro-4-morpholino-6-(3-thiazolidinyl)-1,3,5-triazine (85.2 mg, 0.296 mmol) was dissolved in DMF (2 ml), added with sodium hydroxide (23.7 mg, 0.593 mmol) and imidazole (43.4 mg, 0.637 mmol) and stirred at 110° C.-120° C. for 30 minutes. The reaction mixture was evaporated under reduced pressure. The obtained residue was added with ethyl acetate and water, and then shaken for mixing. The organic layer was separated from the mixture, washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography, using dichloromethane and methanol (98: 2) as eluant, to obtain 83.7 mg (yield: 88.6%) of the titled compound.

Workup

  1. temperaturecooled to -5° C.-0° C
  2. customwas evaporated under reduced pressure
  3. additionThe residue was added with ethyl acetate and water
  4. stirringshaken
  5. additionfor mixing
  6. customThe organic layer was separated from the mixture
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customThe residue obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8a06d268e824f698da6f2a3fb6fd1cf
Source dataset
uspto-grants-1996_02
Patent number
US05489591

Reaction notes

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