2-Butanethiol → HCID 178456540, compound

HRID 373231Notes

Reaction equation

HRID 373231 reaction equation
[Cl:1][C:2]1[C:3](=[O:50])[N:4]([CH2:47][CH2:48][CH3:49])[C:5](=[O:46])[N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]=1Cl.[CH:51]([SH:55])([CH2:53][CH3:54])[CH3:52].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:3](=[O:50])[N:4]([CH2:47][CH2:48][CH3:49])[C:5](=[O:46])[N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:14][CH:15]=2)[C:7]=1[S:55][CH:51]([CH3:52])[CH2:53][CH3:54]

Participants

5

Reactant 3

HCID 105602-ButanethiolHCID 11430Potassium CarbonateHCID 19811540HCID 19811540, compound

Product 1

HCID 178456540HCID 178456540, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5,6-dichloro-3-propyl-1-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]pyrimidine-2,4(1H,3H)-dione (0.22 g), sec-butylmercaptan (0.04 g) and potassium carbonate (0.09 g) in acetonitrile (5 ml) was heated under reflux for 4 hours. The reaction mixture was concentrated to dryness. The resulting residue was dissolved in methanol (15 ml) and 1N hydrochloric acid (1.5 ml) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated to dryness and then the residue was extracted with methylene chloride-water. The organic layer was washed with water, dried, and evaporated to dryness. The resulting residue was purified by column chromatography on silica gel to give yellow amorphous powders (90 mg, 56%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionThe resulting residue was dissolved in methanol (15 ml)
  5. concentrationThe reaction mixture was concentrated to dryness
  6. extractionthe residue was extracted with methylene chloride-water
  7. washThe organic layer was washed with water
  8. customdried
  9. customevaporated to dryness
  10. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c8ea2189ee6b4b61903cdd22a0f5e1ca
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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