Triethylamine → HCID 15053460, compound

HRID 2081467Notes

Reaction equation

HRID 2081467 reaction equation
C(O)(=O)C(O)=O.[O:7]([CH:14]1[CH2:17][NH:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+]([NH:21][C:22](N)=[O:23])([O-])=O.C(N(CC)CC)C>CC(C)=O.O>[O:7]([CH:14]1[CH2:17][N:16]([C:22]([NH2:21])=[O:23])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62372NitroureaHCID 19799622HCID 19799622, compound

Product 1

HCID 15053460HCID 15053460, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A stirred slurry of 7 g (0.03 mole) of 3-phenoxyazetidine oxalate [1:1] in 100 ml of acetone was treated with 5.3 g (0.05 mole) of nitrourea then after 30 min, treated with 5 ml of water and 5 ml of triethylamine. After stirring for 8 hr, the reaction mixture was diluted with 125 ml of water and stirred until a fine white crystalline solid precipitated. Filtration yielded 3.85 g, m.p. 179°-186° C. The solid was recrystallized from tetrahydrofuran to yield 1.3 g (22.5%) of fine white crystals, m.p. 195°-196° C.

Workup

  1. stirringstirred until a fine white crystalline solid
  2. customprecipitated
  3. filtrationFiltration
  4. customyielded 3.85 g, m.p. 179°-186° C
  5. customThe solid was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-4c9bf4c155144d33875a13142564d68c
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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