Toluene → HCID 15610794, compound

HRID 1607550Notes

Reaction equation

HRID 1607550 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 spray dry 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 elutant. Thus 3.0 g of 6-chloro-7-fluoro-2-hexylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained.

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-d23c1c39061e4e7a9ed9cf51b5b4807a
Source dataset
uspto-grants-1989_09
Patent number
US04866064

Reaction notes

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