Ethyl Bromide → 3-ethyl-1-(4-nitrophenyl)-2,4(1H,3H)-pyrimidinedione

HRID 2106764Notes

Reaction equation

HRID 2106764 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]2=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].Br[CH2:21][CH3:22]>CN(C)C(=O)C>[CH2:21]([N:12]1[C:13](=[O:16])[CH:14]=[CH:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[C:11]1=[O:17])[CH3:22]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 112763381-(4-Nitrophenyl)pyrimidine-2,4-dione

Product 1

HCID 151254793-ethyl-1-(4-nitrophenyl)-2,4(1H,3H)-pyrimidinedioneYield 65.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A mixture of 3 parts of 1-(4-nitrophenyl)-2,4(1H,3H)-pyrimidinedione, 1,4 parts of potassium hydroxide and 67.5 parts of N,N-dimethylacetamide was stirred for 1 hour at room temperature under nitrogen atmosphere. 1.52 Parts of bromoethane were added and stirring was continued overnight at room temperature. The reaction mixture was poured into 100 parts of ice water. The product was filtered off and stirred in methanol. The product was filtered off and dried in vacuo at 60° C., yielding 2.4 parts (65.6%) of 3-ethyl-1-(4-nitro-phenyl)-2,4(1H,3H)-pyrimidinedione; mp. 182.5° C. (int. 24).

Workup

  1. stirringstirring
  2. waitwas continued overnight at room temperature
  3. filtrationThe product was filtered off
  4. stirringstirred in methanol
  5. filtrationThe product was filtered off
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-d072a9a384e947f2a9bfee02dda21a87
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

Loading…