Diethyl Ether → HCID 19978212, compound

HRID 1449532Notes

Reaction equation

HRID 1449532 reaction equation
[ClH:1].[CH3:2][C:3]1[N:7]2[CH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][N:11]=[C:6]2[S:5][C:4]=1[C:14]([OH:16])=O.C(OCC)C>S(Cl)(Cl)=O>[ClH:1].[CH3:2][C:3]1[N:7]2[CH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][N:11]=[C:6]2[S:5][C:4]=1[C:14]([Cl:1])=[O:16]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 67715282HCID 67715282, compound

Product 1

HCID 19978212HCID 19978212, compoundYield 198.1%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

In 6 ml of thionylchloride was suspended 1.0 g of 3,6,6-trimethyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carboxylic acid hydrochloride obtained in Example 120, followed by reflux under heating for 30 minutes. After dissolving completely, the mixture was cooled. Under cooling with ice, to the mixture was added anhydrous diethylether. The precipitated crystals were collected by filtration and dried under reduced pressure to obtain 1.06 g of 3,6,6-trimethyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride. The total amount of this compound and 610 mg of 3,5-dimethylaniline was dissolved in the mixture 60 ml of pyridine and 10 ml of dimethylformamide, followed by stirring at 60° C. for 17 hours. The reaction mixure was concentrated and to the concentrate was added 5% sodium hydrogencarbonate aqueous solution. The precipitated crystals were collected by filtration and washed diethylether. The obtained powder was suspended in diethylether. To the suspension was added 0.2 ml of saturated hydrogenchloride dioxane solution, followed by stirring at room temperature. The precipitated crystals were collected by filtration. The crystals were recrystallized from a mixed solvent of ethanol and diethylether to obtain 810 mg of the titled compound.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 30 minutes
  3. dissolutionAfter dissolving completely
  4. temperaturethe mixture was cooled
  5. temperatureUnder cooling with ice, to the mixture
  6. filtrationThe precipitated crystals were collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-50bcb20476544076bf6a6623bac64b83
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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