1,3-Propanediamine → 2-Diphenylmethylamino-1,4,5,6-tetrahydropyrimidine hydroiodide

HRID 46637

Reaction equation

HRID 46637 reaction equation
[IH:1].[C:2]1([CH:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:9][C:10](=[NH:13])SC)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][CH2:21][CH2:22][CH2:23]N>ClC1C=CC=CC=1Cl>[IH:1].[C:2]1([CH:8]([NH:9][C:10]2[NH:20][CH2:21][CH2:22][CH2:23][N:13]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 178504030HCID 178504030, compound

Product 1

HCID 202981782-Diphenylmethylamino-1,4,5,6-tetrahydropyrimidine hydroiodideYield 62.6%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To 38.43 grams (0.10 mole) of 1-diphenylmethyl-2-methyl-2-thiopseudourea hydroiodide in 25 milliliters of o-dichlorobenzene was added 7.41 grams (0.10 mole) of 1,3-diaminopropane, and the mixture heated (below reflux temperature) for four hours with stirring; then the temperature was increased to reflux temperature and maintained under reflux for 12 hours. The mixture was allowed to cool to room temperature, the solvent decanted off and the residue dissolved in methanol. The methanol solution was concentrated while simultaneously adding isopropanol to obtain 24.6 grams (62.6 percent yield) of 2-diphenylmethylamino-1,4,5,6-tetrahydropyrimidine hydroiodide product, m.p. (185° C.) 197°-200° C. After two recrystallizations from methanol-isopropanol, a purified product of melting point 207°-209° C. was obtained.

Workup

  1. temperaturethe mixture heated
  2. temperature(below reflux temperature) for four hours
  3. temperaturethen the temperature was increased
  4. temperatureto reflux temperature
  5. temperaturemaintained
  6. temperatureunder reflux for 12 hours
  7. customthe solvent decanted off
  8. dissolutionthe residue dissolved in methanol
  9. concentrationThe methanol solution was concentrated while simultaneously adding isopropanol

Sources & evidence

ORD record
ord-5efb8ff247b54fbc8df6179cc291bc73
Source dataset
uspto-grants-1979_11
Patent number
US04174401

Linked notes

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