Ammonium thiocyanate → HCID 178521083, compound

HRID 922710Notes

Reaction equation

HRID 922710 reaction equation
Cl.O[CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[NH2:5].[S-:14][C:15]#[N:16].[NH4+]>O>[SH:14][C:15]1[NH:16][CH:3]=[C:4]([C@@H:6]([OH:7])[C@H:8]([OH:9])[C@H:10]([OH:11])[CH2:12][OH:13])[N:5]=1

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 2723635(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

Product 1

HCID 178521083HCID 178521083, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
84.5 °C

Procedure

To glucosamine hydrochloride (200 g, 0.928 mol) were added water (300 mL) and ammonium thiocyanate (212 g, 2.78 mol, 3.0 equivalents) at 25° C., and the mixture was stirred at 80 to 89° C. for 8 hr. The reaction mixture was allowed to cool to 60° C., water (300 mL) and seed crystals were added thereto, and the mixture was stirred at 25 to 40° C. for 15 hr. The crystals were collected by filtration, washed twice with water (100 mL), and vacuum-dried (50° C.) to a constant amount to give (1R,2S,3R)-1-(2-sulfanyl-1H-imidazol-4-yl)butane-1,2,3,4-tetraol (101.4 g). yield 50%.

Workup

  1. temperatureto cool to 60° C.
  2. stirringthe mixture was stirred at 25 to 40° C. for 15 hr
  3. filtrationThe crystals were collected by filtration
  4. washwashed twice with water (100 mL)
  5. customvacuum-dried (50° C.) to a constant amount

Sources & evidence

ORD record
ord-01fa24a65bfc4cde93e522f09e0bf815
Source dataset
uspto-grants-2016_03
Patent number
US09278938B2

Reaction notes

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