1,1'-Carbonyldiimidazole → 1-Phenyltetrahydropyrimidin-2(1H)-one

HRID 1956365Notes

Reaction equation

HRID 1956365 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13]>O1CCCC1>[C:1]1([N:7]2[CH2:8][CH2:9][CH2:10][NH:11][C:12]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 427260N-(3-aminopropyl)aniline

Product 1

HCID 15144201-Phenyltetrahydropyrimidin-2(1H)-oneYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.5 g (16.5 mM) of N1 -phenylpropane-1,3-diamine are dissolved in 56.5 ml of anhydrous tetrahydrofuran. A mixture of 3.8 g (23.3 mM) of carbonyldiimidazole in 115 ml of anhydrous tetrahydrofuran is poured into the solution, and the mixture is left at room temperature overnight. The mixture is concentrated, taken up in ethyl acetate, washed with normal HCl and dried over MgSO4 to yield 2 g of a white solid that melts at 210°-211° C. and corresponds to the expected product.

Workup

  1. additionis poured into the solution
  2. concentrationThe mixture is concentrated
  3. washwashed with normal HCl
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e27d4ff5a87f4a10b07309ced22c6931
Source dataset
uspto-grants-1998_07
Patent number
US05780474

Reaction notes

Loading…