Process for making imidazolines and tetrahydropyrimidines from oxazolines and alkylenediamines

{
  "publication_number": "US4014880A",
  "country": "US",
  "kind": "A",
  "title": "Process for making imidazolines and tetrahydropyrimidines from oxazolines and alkylenediamines",
  "abstract": "The reaction of 2-oxazolines with 1,2- or 1,3-alkylenediamines to form 2-imidazolines or 1,4,5,6-tetrahydropyrimidines is catalyzed by Lewis acids.",
  "claims": [
    "1. In the method of preparing a 2-imidazoline or a 1,4,5,6-tetrahydropyrimidine by reacting (a) a 2-oxazoline with (b) 1,2-alkylenediamine or a 1,3-alkylenediamine in liquid-phase, the improvement comprising conducting the reaction in the presence of a small but sufficient amount of a Lewis acid to catalyze the reaction between (a) and (b).",
    "2. The process defined by claim 1 wherein the oxazoline reactant is of the formula ##STR4## wherein R is alkyl, aryl, or inertly-substituted alkyl or aryl and R 1 -R 4 are each independently hydrogen, lower alkyl or hydroxy-substituted lower alkyl.",
    "3. The process defined by claim 2 wherein R is alkyl of from 1 to about 20 carbon atoms and R 1 -R 4 are each hydrogen.",
    "4. The process defined by claim 1 wherein reactant (b) is of the formula R.sub.5 --NH--CHR.sub.6 CH.sub.2 n NH.sub.2, wherein R 5 is hydrogen, lower alkyl or inertly-substituted lower alkyl; R 6 is hydrogen or lower alkyl; and n is 1 or 2.",
    "5. The process defined by claim 4 wherein R 5 is hydrogen and R 6 is hydrogen, methyl or ethyl.",
    "6. The process defined by claim 4 wherein n is 1.",
    "7. The process defined by claim 1 wherein the catalyst is of the formula CrCl.sub.2.sup.. 6H.sub.2 O; MoO.sub.2; H.sub.2 WO.sub.3; Zn(OAc).sub.2.sup.. 2H.sub.2 O; CdCl.sub.2.sup.. 2.5H.sub.2 O; HgCl.sub.2; or AlCl.sub.3.",
    "8. The process defined by claim 7 wherein (a) is 2-ethyl-2-oxazoline and (b) is 1,2-ethylenediamine or 1,3-propylenediamine.",
    "9. The process defined by claim 1 wherein (a) is 2-methyl-2-oxazoline, 2-ethyl-2-oxazoline, 2,5-dimethyl-2-oxazoline, or 2-undecyl-2oxazoline (b) is 1,2-ethylenediamine, 1,3-propylenediamine or N-hydroxyethyl ethylenediamine and the Lewis acid catalyst is zinc acetate dihydrate."
  ],
  "cpc": [
    "C07D 239/06",
    "C07D 233/06"
  ],
  "assignees": [
    "DOW CHEMICAL CO"
  ],
  "filing_date": "1976-02-09",
  "publication_date": "1977-03-29",
  "grant_date": "1977-03-29",
  "priority_date": "1976-02-09",
  "application_number": "US-65655876-A",
  "family_id": "24633561",
  "citations": [
    "DE2154948A1"
  ]
}