1,2-Dichlorobenzene → 2-Diphenylmethylimino-1,2,3,4,5,6-hexahydro-1,3-dimethylpyrimidine hydroiodide

HRID 225113Notes

Reaction equation

HRID 225113 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.[CH3:20][NH:21][CH2:22][CH2:23][CH2:24]NC.Cl[C:28]1C=CC=CC=1Cl>>[IH:1].[C:2]1([CH:8]([N:9]=[C:10]2[N:21]([CH3:20])[CH2:22][CH2:23][CH2:24][N:13]2[CH3:28])[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 3

HCID 72391,2-DichlorobenzeneHCID 66978N,N'-Dimethyl-1,3-propanediamineHCID 178504030HCID 178504030, compound

Product 1

HCID 202981422-Diphenylmethylimino-1,2,3,4,5,6-hexahydro-1,3-dimethylpyrimidine hydroiodideYield 59.8%

Procedure

To 38.43 grams (0.10 mole) of 1-diphenylmethyl-2-methyl-2-thiopseudourea hydroiodide in 200 milliliters of o-dichlorobenzene was added 10.22 grams (0.10 mole) of N,N'-dimethyl-1,3-propanediamine and the resulting mixture heated under reflux for 21 hours. The reaction mixture was cooled, the solvent decanted therefrom and isopropanol added to the gummy residue to obtain 24.35 grams (59.8 percent yield) of 2-diphenylmethylimino-1,2,3,4,5,6-hexahydro-1,3-dimethylpyrimidine hydroiodide product of m.p., 215°-219° C. After two recrystallizations from methanol-isopropanol, a purified product, m.p. 221° C., was obtained.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 21 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent decanted
  5. additionisopropanol added to the gummy residue

Sources & evidence

ORD record
ord-a50227786539463692989c540d926bcb
Source dataset
uspto-grants-1980_11
Patent number
US04235894

Reaction notes

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