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Sulfolane → 7-fluoro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

HRID 1607542
Notes
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Reaction equation

HRID 1607542 reaction equation
Cl[C:2]1[N:3]=[C:4]2[S:12][C:11]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:10][N:5]2[C:6](=[O:9])[C:7]=1[CH3:8].[F-:21].[K+].S1(CCCC1)(=O)=O>O>[F:21][C:2]1[N:3]=[C:4]2[S:12][C:11]([S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[N:10][N:5]2[C:6](=[O:9])[C:7]=1[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 522689Potassium FluorideHCID 156107877-chloro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 156107887-fluoro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-oneYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.6 g of the thus obtained 7-chloro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one, 3.0 g of spray dry potassium fluoride and 32 ml of sulfolane was heated at 205°~225° C. in a stream of nitrogen for 1 and half hours. After cooling, water was added to the mixture, and the mixture was extracted with toluene. The toluene layer was collected and washed with water. The toluene phase was dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by column chromatography on a silica gel with an ethyl acetate/n-hexane (1:3) mixture as an eluent. After the solvent was distilled off, 5.2 g of 7-fluoro-2-heptylthio-6-methyl-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with toluene
  3. customThe toluene layer was collected
  4. washwashed with water
  5. dry with materialThe toluene phase was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by column chromatography on a silica gel with an ethyl acetate/n-hexane (1:3) mixture as an eluent
  8. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-3046aa2508d84d808d12a9b66cee2428
Source dataset
uspto-grants-1989_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04866064

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes