Diethyl Ether → HCID 19978193, compound

HRID 1449515Notes

Reaction equation

HRID 1449515 reaction equation
[ClH:1].[CH:2]([C:5]1[N:9]2[CH2:10][CH2:11][CH2:12][N:13]=[C:8]2[S:7][C:6]=1[C:14]([OH:16])=O)([CH3:4])[CH3:3].C(OCC)C>S(Cl)(Cl)=O>[ClH:1].[CH:2]([C:5]1[N:9]2[CH2:10][CH2:11][CH2:12][N:13]=[C:8]2[S:7][C:6]=1[C:14]([Cl:1])=[O:16])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 67715066HCID 67715066, compound

Product 1

HCID 19978193HCID 19978193, compoundYield 201.3%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

In 50 ml of thionylchloride was suspended 6.5 g of 3-isopropyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carboxylic acid hydrochloride obtained in Example 46, followed by reflux under heating for 1 hour. To the reaction mixture was added dry diethylether. The precipitated crystals were collected by filtration and washed with diethylether to obtain 7.0 g of 3-isopropyl-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-2-carbonylchloride hydrochloride. In the mixture 5 ml of pyridine and 5 ml of dimethylformamide was dissolved 500 mg of this compound. To the solution was added 291 mg of 2,5-dimethoxyaniline, followed by stirring at 80uÅ for 12 hours. The solvent was removed under reduced pressure. The residue was crystallized from isopropylalcohol and diethylether. The resulting crystals were recrystallized from isopropylalcohol and saturated hydrogenchloride diethylether solution to obtain 200 mg of the titled compound.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 1 hour
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with diethylether

Sources & evidence

ORD record
ord-be4b2cd657364358bb621d2e70dc002d
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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