Sodium Hydroxide → N-(1,4,5,6-tetrahydropyrimidin-2-yl)-N'-(2-trifluoromethylphenyl)urea monohydrochloride hydrate

HRID 358343Notes

Reaction equation

HRID 358343 reaction equation
[ClH:1].[NH2:2][C:3]1[NH:4][CH2:5][CH2:6][CH2:7][N:8]=1.[OH-].[Na+].[O-:11]S([O-])(=O)=O.[Na+].[Na+].C[C:19]1[C:20]([C:28]([F:31])([F:30])[F:29])=[C:21]([N:25]=[C:26]=[O:27])[CH:22]=[CH:23][CH:24]=1>C1COCC1>[OH2:11].[ClH:1].[NH:8]1[CH2:7][CH2:6][CH2:5][N:4]=[C:3]1[NH:2][C:26]([NH:25][C:21]1[CH:22]=[CH:23][CH:24]=[CH:19][C:20]=1[C:28]([F:29])([F:30])[F:31])=[O:27]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 225575271,3-Diazinan-2-imine hydrochlorideHCID 53958223Methyl-2-trifluoromethylphenyl isocyanate

Product 1

HCID 12790789N-(1,4,5,6-tetrahydropyrimidin-2-yl)-N'-(2-trifluoromethylphenyl)urea monohydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 9.90 g (0.073 mol) of 2-amino-1,4,5,6-tetrahydropyrimidine hydrochloride, 6.0 g (0.075 mol) of 50% NaOH and 75 ml of THF was stirred for 0.75 hours at room temperature and then 10 g. Na2SO4 was added. After stirring for 0.5 hours, a solution of 9.36 g. (0.050 mol) of methyl-2-trifluoromethylphenyl isocyanate in 50 ml of THF was added over a period of 0.5 hours. After stirring for 1 hour, the reaction mixture was filtered, the filtrate evaporated in vacuo and the residue dissolved in 50 ml of 10% HCl and 100 ml of H2O with warming. After filtration through a pad of diatomaceous earth, chilling in ice gave the crystalline hydrychloride which was recrystallized from hot H2O affording 10.09 g (63%). This material was dried to constant weight in vacuo (20° C., 5 mm Hg) to give pure N-(1,4,5,6 -tetrahydropyrimidin-2-yl)-N'-(2-trifluoromethylphenyl)urea monohydrochloride hydrate; m.p. (120) 182.5°-184.5° C. IR(CHCl3) 3240 (br), 1717, 1642, 1594 cm-1 ; UV max. (MeOH) 281 infl (ε6,900), 256 nm (ε29,000) and 215 nm (ε14,900).

Workup

  1. stirringAfter stirring for 0.5 hours
  2. stirringAfter stirring for 1 hour
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate evaporated in vacuo
  5. dissolutionthe residue dissolved in 50 ml of 10% HCl
  6. temperature100 ml of H2O with warming
  7. filtrationAfter filtration through a pad of diatomaceous earth
  8. temperaturechilling in ice
  9. customgave the crystalline hydrychloride which
  10. customwas recrystallized from hot H2O affording 10.09 g (63%)
  11. customThis material was dried to constant weight in vacuo (20° C., 5 mm Hg)

Sources & evidence

ORD record
ord-576f27ae1f3f4a51b377483ff66ec2a8
Source dataset
uspto-grants-1984_08
Patent number
US04466966

Reaction notes

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