N-bromobutanimide → HCID 19744480, compound

HRID 2254467Notes

Reaction equation

HRID 2254467 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1C=C(C(OCC)=O)C=CN=1)C.CC(C)(C)C#C/C=C/CN(C[C:35]1[O:39][N:38]=[C:37]([C:40]([O:42]CC)=O)[CH:36]=1)CC.CC1ON=C(C(OCC)=O)C=1.BrN1C(=O)CCC1=O.C(NC/C=C/C#CC(C)(C)C)C>>[CH3:1][C:2]([CH3:22])([CH3:23])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([C:35]1[O:39][N:38]=[C:37]([CH:40]=[O:42])[CH:36]=1)[CH2:10][CH3:11]

Participants

6

Reactant 5

HCID 67184N-bromobutanimideHCID 76677Ethyl 5-methylisoxazole-3-carboxylateHCID 10909912HCID 10909912, compoundHCID 19744650HCID 19744650, compoundHCID 19744842HCID 19744842, compound

Product 1

HCID 19744480HCID 19744480, compound

Procedure

The same reaction as in Referential Example 49 is carried out except that instead of the starting (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-4-ethoxycarbonyl-2-pyridylmethylamine, (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-ethoxycarbonyl-5-isoxazolylmethylamine [synthesized by brominating ethyl 5-methylisoxazole-3-carboxylate with N-bromosuccinimide and condensing the brominated product with (E)-N-ethyl-6,6-dimethyl-2-hepten-4-ynylamine] is used, (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-formyl-5-isoxazolylamine is obtained.

Workup

  1. customThe same reaction as in Referential Example 49
  2. customsynthesized

Sources & evidence

ORD record
ord-fc8089837db44d52b254713d6e2cde22
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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