Water → HCID 10043399, compound

HRID 255729Notes

Reaction equation

HRID 255729 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([C:10](=[CH:16]N(C)C)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[C:23]([NH2:31])(=[NH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.O>C(O)CCC>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][N:31]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:30]=2)=[CH:20][CH:21]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 80289Benzamidine, hydrochlorideHCID 54398161Ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoate

Product 1

HCID 10043399HCID 10043399, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 2-(4-nitrobenzoyl)-3-dimethylaminopropenoate (3 g), benzamidine hydrochloride (1.93 g) and triethylamine (2 ml) in n-butyl alcohol (30 ml) was refluxed for 30 min. The reaction mixture was poured into water (300 ml) and the precipitate was collected by filtration. The residue was recrystallized with diethyl ether to afford ethyl 4-(4-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (3.1 g).

Workup

  1. temperaturewas refluxed for 30 min
  2. filtrationthe precipitate was collected by filtration
  3. customThe residue was recrystallized with diethyl ether

Sources & evidence

ORD record
ord-93a816eab299408e94a16be5dd9a8c34
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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