Toluene → HCID 15610794, compound

HRID 1073792Notes

Reaction equation

HRID 1073792 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]2[N:9]=[C:10]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[S:11][C:5]2=[N:4][C:3]=1Cl.[F-:20].[K+].S1(CCCC1)(=O)=O.C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[C:7](=[O:8])[N:6]2[N:9]=[C:10]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[S:11][C:5]2=[N:4][C:3]=1[F:20]

Participants

6

Reactant 4

HCID 1140TolueneHCID 31347SulfolaneHCID 522689Potassium FluorideHCID 15610793HCID 15610793, compound

Product 1

HCID 15610794HCID 15610794, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4.4 g of the thus obtained 6,7-dichloro-2-hexylthio-5H-1,3,4-thiadiazolo[3,2-a]-pyrimidin-5-one, 2.2 g of potassium fluoride and 20 ml of sulfolane was heated to 185°~200° C. and stirred for 45 minutes. After cooling, toluene and water were added to the reaction solution and extraction was carried out. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was separated by silica gel column chromatography using an ethyl acetate/toluene mixture as an eluent. Thus 3.0 g of 6-chloro-7-fluoro-2-hexylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. m.p. 105°~111° C. Yield 71%.

Workup

  1. temperatureAfter cooling
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-5c3730f268f34ac3a6941257bd68c918
Source dataset
uspto-grants-1990_11
Patent number
US04971971

Reaction notes

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