Ammonia → Sec.-butyl 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-5-(3-benzyl-1,2,4-oxadiazol-5-yl)pyridine-3-carboxylate

HRID 637727Notes

Reaction equation

HRID 637727 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:11]([C:15]1[N:19]=[CH:18][O:17][N:16]=1)[C:12]([CH3:14])=O.[C:20]([O:26][CH:27]([CH2:29][CH3:30])[CH3:28])(=[O:25])[CH2:21][C:22]([CH3:24])=O.[NH3:31]>C(O)C>[CH3:24][C:22]1[NH:31][C:7]([CH3:8])=[C:6]([C:18]2[O:17][N:16]=[C:15]([CH2:11][C:12]3[CH:4]=[CH:3][CH:2]=[CH:9][CH:14]=3)[N:19]=2)[CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=2[Cl:1])[C:21]=1[C:20]([O:26][CH:27]([CH2:29][CH3:30])[CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 357452,3-DichlorobenzaldehydeHCID 139498sec-Butyl acetoacetateHCID 201305023-Acetonyl-1,2,4-oxadiazole

Product 1

HCID 137175491Sec.-butyl 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-5-(3-benzyl-1,2,4-oxadiazol-5-yl)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.75 g of 2,3-dichlorobenzaldehyde, 2.2 g of 3-acetonyl-1,2,4-oxadiazole, 1.6 g of sec.-butyl acetoacetate and 1.2 g of 25% strength aqueous ammonia solution in 50 ml of ethanol are heating to boiling for 6 hours. After concentrating, there remains an oily residue which is triturated with ether/petroleum ether and gradually crystallises. The resulting solid is then recrystallised from ethyl acetate/isopropanol: melting point=116° to 117° C.

Workup

  1. concentrationAfter concentrating
  2. customis triturated with ether/petroleum ether
  3. customgradually crystallises
  4. customThe resulting solid is then recrystallised from ethyl acetate/isopropanol

Sources & evidence

ORD record
ord-4feb367cf1c34b64961cea83fad1fe38
Source dataset
uspto-grants-1985_12
Patent number
US04558058

Reaction notes

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