Triethylamine → HCID 178469226, compound

HRID 255702Notes

Reaction equation

HRID 255702 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=2[CH:10]=[C:11]([C:17]([CH3:19])=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.Cl.[C:27]([NH2:30])(=[NH:29])[CH3:28].C(N(CC)CC)C.C(OCC)(=O)C>C(O)CCC>[ClH:1].[CH3:28][C:27]1[NH:30][CH:10]([C:9]2[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=2[O:7][CH2:6][C:5]2[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:17]([CH3:19])[N:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67170Acetamidine monohydrochlorideHCID 53728539HCID 53728539, compound

Product 1

HCID 178469226HCID 178469226, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 2-[2-(4-chlorobenzyloxy)-benzylidene]acetoacetate (10 g), acetamidine hydrochloride (3.16 g), and triethylamine (4.23 g) in n-butanol (100 ml) was refluxed for 3.5 hours. The reaction mixture, added ethyl acetate (100 ml), was washed with water (100 ml) and 5% hydrochloric acid (100 ml) successively. The solvent was evaporated and the residual crystalline was stirred with ethyl acetate (50 ml) for 1 hour. The crystals were collected by filtration dried in vacuo to afford ethyl 2,4-dimethyl-6-[2-(4-chlorobenzyloxy)phenyl]-1,6-dihydro-5-pyrimidinecarboxylate hydrochloride (2.45 g).

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. washwas washed with water (100 ml) and 5% hydrochloric acid (100 ml) successively
  3. customThe solvent was evaporated
  4. filtrationThe crystals were collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-f82721d3f1324aee85350dc62d2414b7
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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