Methane → HCID 178512685, compound

HRID 280744Notes

Reaction equation

HRID 280744 reaction equation
S(=O)(=O)(O)O.[N+]([O-])([O-])=O.[Na+].[PH2](O)=O.Cl.Cl.[NH:16]([C:20]1[S:21][CH:22]=[C:23]([C:25]([C:27]2[N:28]=[C:29](N)[NH:30][CH:31]=2)=[O:26])[N:24]=1)[C:17]([NH2:19])=[NH:18].C(=O)([O-])[O-].[Na+].[Na+].C>O.CO>[NH:16]([C:20]1[S:21][CH:22]=[C:23]([C:25]([C:27]2[N:28]=[CH:29][NH:30][CH:31]=2)=[O:26])[N:24]=1)[C:17]([NH2:19])=[NH:18]

Participants

9

Reactant 6

HCID 297MethaneHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 24268Sodium NitrateHCID 4124402Phosphinic AcidHCID 178478804HCID 178478804, compound

Product 1

HCID 178512685HCID 178512685, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

A mixture of 42 ml of concentrated sulfuric acid and 21 ml of water was cooled to -10° and 1.56 g (22.7 mmol) of sodium nitrate was added. Afrer stirring at -5° for ten minutes, 8.1 ml (78 mmol) of cold 50% hypophosphorous acid was added and stirring was continued for another 10 minutes at -5°. A solution of 2.5 g (8.4 mmol) of 2-guanidino-4-(2-amino- 4-imidazoyl)thiazole dihydrochloride in 100 ml of water was added dropwise over 0.5 hour. The reaction was stirred at 50° for 2 hours, then at room temperature for 16 hours. The reaction mixture was diluted with 500 ml of water, made basic with solid sodium carbonate and extracted three times with 150 ml portions of ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulfate, filtered, and evaporated leaving a solid. This solid was taken up into boiling methanol, decolorized with charcoal, and concentrated to a small volume. The resulting solid was collected and dried, thereby affording 90 mg (5%) of 2-guanidino-4-(4-imidazoyl)thiazole identical to the material of Example 31 by thin layer chromatography and high resolution mass spectrometry.

Workup

  1. temperaturewas cooled to -10°
  2. stirringstirring
  3. stirringThe reaction was stirred at 50° for 2 hours
  4. waitat room temperature for 16 hours
  5. extractionextracted three times with 150 ml portions of ethyl acetate
  6. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customleaving a solid
  10. concentrationconcentrated to a small volume
  11. customThe resulting solid was collected
  12. customdried

Sources & evidence

ORD record
ord-a8f3e8f973ed4595bfb1375bb888cc75
Source dataset
uspto-grants-1986_05
Patent number
US04590299

Reaction notes

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