Phenyl Isothiocyanate → HCID 178521069, compound

HRID 2092909Notes

Reaction equation

HRID 2092909 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]2[OH:9])[CH:5]=[N:4][C:3]=1[C:16]([NH2:18])=[O:17].C1(N=[C:26]=[S:27])C=CC=CC=1>N1C=CC=CC=1>[SH:27][C:26]1[N:18]=[C:16]([OH:17])[C:3]2[N:4]=[CH:5][N:6]([C:2]=2[N:1]=1)[C@@H:7]1[O:13][C@H:12]([CH2:14][OH:15])[C@@H:10]([OH:11])[C@H:8]1[OH:9]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 17513Acadesine

Product 1

HCID 178521069HCID 178521069, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The 5-Amino-1-β-ribofuranosylimidazole-4-carboxamide (1.3 g, 5 mmol) was dissolved in pyridine and 18 ml (15 mmol) phenyl-isothiocyanate were added slowly. The reaction mixture was refluxed for 2 hours under argon atmosphere. The solution was cooled to room temperature, the precipitate collected by filtration and washed with diethyl ether. The obtained pyridinium salt of the product was dissolved in aqueous sodium hydroxide (15%, 40 ml). The solution was heated 30 minutes at 60° C. and concentrated under vacuum. Methanol was then added and the solution was kept in the refrigerator overnight. After 20 hours the precipitated colourless prisms were collected by filtration to give 1.2 g (80%) 2-Mercaptoinosine.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours under argon atmosphere
  2. filtrationthe precipitate collected by filtration
  3. washwashed with diethyl ether
  4. dissolutionThe obtained pyridinium salt of the product was dissolved in aqueous sodium hydroxide (15%, 40 ml)
  5. temperatureThe solution was heated 30 minutes at 60° C.
  6. concentrationconcentrated under vacuum
  7. additionMethanol was then added
  8. customwas kept in the refrigerator overnight
  9. filtrationAfter 20 hours the precipitated colourless prisms were collected by filtration

Sources & evidence

ORD record
ord-914e5a6ace3446ff9ba6acb0a8402ae0
Source dataset
uspto-grants-2013_05
Patent number
US08440812B2

Reaction notes

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