Ammonia → HCID 178433513, compound

HRID 1075158Notes

Reaction equation

HRID 1075158 reaction equation
N.C(=O)([O-])[O-].[Na+].[Na+].[Cl:8][C:9]1[C:10](=S)[NH:11][C:12](=[O:16])[NH:13][C:14]=1[CH3:15]>O.[Ni]>[CH3:15][C:14]1[C:9]([Cl:8])=[CH:10][NH:11][C:12](=[O:16])[N:13]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 20494272HCID 20494272, compound

Product 1

HCID 178433513HCID 178433513, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

Conc. aqueous ammonia (200 ml) and sodium carbonate (0.012 mol) were added to Raney-Ni (20 g) in water (200 ml) followed by the addition of 5-chloro-6-methyl-4-thiouracil (0.023 mol). The reaction mixture was stirred at room temperature for 1 hr and then heated under reflux for 3 hr. The catalyst was removed from the cold reaction mixture and the filtrate evaporated. The residual material was stirred in 5 N NaOH (20 ml) and the sodium salt filtered off from the ice-cold mixture and washed with abs. ethanol and acetone. The product was recrystallised from aqueous ethanol; yield 53%, m.p. 300° C. (decomp.); For elemental analysis the sodium salt in aqueous solution was neutralised with HCl. Found: C, 41.40; H, 3.60. Calc. for C5H5ClN2O: C, 41.54; H, 3.48.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hr
  3. customThe catalyst was removed from the cold reaction mixture
  4. customthe filtrate evaporated
  5. stirringThe residual material was stirred in 5 N NaOH (20 ml)
  6. filtrationthe sodium salt filtered off from the ice-cold mixture
  7. washwashed with abs
  8. customThe product was recrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-a124b5eb7c144d98ac21ec9afbba5503
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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