Ammonium Chloride → 4-(pentylamino)-1H-imidazole-5-carbothioamide

HRID 600600Notes

Reaction equation

HRID 600600 reaction equation
[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]#[N:13])[CH2:2][CH2:3][CH2:4][CH3:5].O.O.[SH2:16].[Na].[Cl-].[NH4+]>CO>[CH2:1]([NH:6][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12](=[S:16])[NH2:13])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 451205654-(pentylamino)-1H-imidazole-5-carbonitrileHCID 86584117Sodium hydrogen sulfide dihydrate

Product 1

HCID 598538144-(pentylamino)-1H-imidazole-5-carbothioamideYield 100.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(pentylamino)-1H-imidazole-5-carbonitrile (25 g, 0.14 mol), sodium hydrogen sulfide dihydrate (26 g, 0.28 mol) and ammonium chloride (7.5 g, 0.14 mol) in methanol (400 mL) was stirred at room temperature overnight. The conversion was about 60% according to analytical LCMS. The mixture was then stirred at 50° C. for 3 hours. The methanol was removed and the residue was diluted with water and EtOAc. The organic layer was washed with water and brine respectively, dried and concentrated to yield the crude product (30.0 g), which was used for next step without further purification. LCMS calculated for C9H17N4S (M+H): 213.1. found: 213.1.

Workup

  1. stirringThe mixture was then stirred at 50° C. for 3 hours
  2. customThe methanol was removed
  3. additionthe residue was diluted with water and EtOAc
  4. washThe organic layer was washed with water and brine respectively
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70f0bbfdf973439492f8eeb42badc1e1
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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