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

HRID 1073784
Notes
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Reaction equation

HRID 1073784 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 column 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. m.p. 78°~91° C. Yield 63%.

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 column with an ethyl acetate/n-hexane (1:3) mixture as an eluent
  8. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-480f7532f15b4be5b83f9acd01d4c3bb
Source dataset
uspto-grants-1990_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04971971

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes