Ammonia → Darodipine

HRID 358348Notes

Reaction equation

HRID 358348 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]=O)=[CH:8][CH:7]=[CH:6][C:5]=12.[CH2:12]([O:14][C:15](=[O:20])[CH2:16][C:17]([CH3:19])=O)[CH3:13].[NH3:21]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:10]([C:9]2[C:4]3[C:5](=[N:1][O:2][N:3]=3)[CH:6]=[CH:7][CH:8]=2)[C:16]([C:15]([O:14][CH2:12][CH3:13])=[O:20])=[C:17]([CH3:19])[NH:21][C:17]=1[CH3:19])=[O:20])[CH3:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 8868Ethyl AcetoacetateHCID 102908732,1,3-Benzoxadiazole-4-carbaldehyde

Product 1

HCID 51701Darodipine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 g of 2,1,3-benzoxadiazole-4-aldehyde, 5.7 g of acetoacetic acid ethyl ester, 2.5 ml of concentrated ammonia and 10 ml of ethanol are refluxed for 6 hours. The mixture is subsequently evaporated and the residual oil is chromatographed on silica gel with chloroform/acetic acid ethyl ester (9:1) to yield the title compound. The product is recrystallised from toluene, m.p. 153°-155°.

Workup

  1. customThe mixture is subsequently evaporated
  2. customthe residual oil is chromatographed on silica gel with chloroform/acetic acid ethyl ester (9:1)

Sources & evidence

ORD record
ord-2ec7ca9f28604726b6a49a661f02f296
Source dataset
uspto-grants-1984_08
Patent number
US04466972

Reaction notes

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