Sodium Hydroxide → N-(2,6-Dichlorophenyl)N'-(1,4,5,6-tetrahydropyrimidin-2-yl)urea Monohydrochloride

HRID 358342Notes

Reaction equation

HRID 358342 reaction equation
Cl.[NH2:2][C:3]1[NH:4][CH2:5][CH2:6][CH2:7][N:8]=1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[N:26]=[C:27]=[O:28]>C1COCC1>[ClH:18].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[NH:26][C:27]([NH:2][C:3]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]=1)=[O:28]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 6045371,3-Dichloro-2-isocyanatobenzeneHCID 225575271,3-Diazinan-2-imine hydrochloride

Product 1

HCID 20448671N-(2,6-Dichlorophenyl)N'-(1,4,5,6-tetrahydropyrimidin-2-yl)urea Monohydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 8.50 g (0.0625 mol) of 2-amino-1,4,5,6-tetrahydropyrimidine hydrochloride, 10.0 g (0.12 mol) of 50% NaOH and 70 ml of THF was stirred for 0.5 hours at room temperature and then 10.0 g Na2SO4 was added. After stirring for an additional 0.5 hours, a solution of 9.4 g (0.050 mol) of 2,6-dichlorophenyl isocyanate in 50 ml of THF was added over a period of 1 hour. After stirring for 1 hour, the reaction mixture was filtered, the filtrate evaporated in vacuo and the residue dissolved in 25 ml of 10% HCl and 25 ml of H2O with warming. After filtration through a pad of diatomaceous earth, chilling in ice gave the crystalline hydrochloride which was recrystallized from MeOH-ether affording 12.40 g. This material was ground to a fine powder and dried to constant weight in vacuo (60° C., 5 mm Hg) to give 11.97 g (74%) of the title compound; m.p. 215°-217° C. dec., homogeneous by TLC [5×20 cm silica gel GF CHCl3 --MeOH-NH4OH (90:9:1)]. 1H-NMR (DMSO-d6) 1.85 [pentet, (poorly resolved)2H]; 3.35 (t, J=5 Hz, 4H); 7.2-7.7 (m, 3H); 9.16 (broad s, 2H) exchangeable; 10.02 (broad s, 1H) exchangeable, 11.19 (brS, 1H) exchangeable. IR(KBr) 3125, 1717, 1678, 1678 cm-1 ; UV max. (MeOH) 241 infl. (ε=11,200) and 220 nm infl. (ε=23,500).

Workup

  1. stirringAfter stirring for an additional 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 25 ml of 10% HCl
  6. temperature25 ml of H2O with warming
  7. filtrationAfter filtration through a pad of diatomaceous earth
  8. temperaturechilling in ice

Sources & evidence

ORD record
ord-33139540288d474999706c67901a9b31
Source dataset
uspto-grants-1984_08
Patent number
US04466966

Reaction notes

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