Triethylamine → HCID 70434776, compound

HRID 2308905Notes

Reaction equation

HRID 2308905 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([NH:9][NH2:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[CH2:14][O:13]1.C(N(CC)CC)C.[Cl:27][C:28]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:29]=1[O:30][CH2:31][C:32](Cl)=[O:33]>O1CCCC1>[Cl:2][C:3]1[CH:8]=[C:7]([NH:9][NH:10][C:32]([CH2:31][O:30][C:29]2[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:28]=2[Cl:27])=[O:33])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[CH2:14][O:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69887(2,4-Dichlorophenoxy)acetyl chlorideHCID 13934953HCID 13934953, compound

Product 1

HCID 70434776HCID 70434776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-[(2-chloro-4-hydrazinophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone hydrochloride (1.5 g, 0.0049 mole) and triethylamine (1.4 ml) in tetrahydrofuran (100 ml) was cooled to 10° C. and 2,4-dichlorophenoxyacetyl chloride (0.80 g, 0.0067 mole) was added in one portion. The reaction mixture was stirred overnight at ambient temperature. Triethylamine hydrochloride was removed by filtration, and the filtrate concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with 60:40 ethyl acetate:heptane. Appropriate fractions were combined and concentrated under reduced pressure. The residual solid was recrystallized from ethyl acetate:heptane to yield 2-[[2-chloro-4-[(2,4-dichlorophenoxy)methylcarbonylhydrazo]phenyl]methyl]-4,4-dimethyl-3-isoxaolidinone as a yellow solid; m.p. 149°-150° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customTriethylamine hydrochloride was removed by filtration
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel
  4. washeluting with 60:40 ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. customThe residual solid was recrystallized from ethyl acetate
  7. customheptane to yield 2-[[2-chloro-4-[(2,4-dichlorophenoxy)methylcarbonylhydrazo]phenyl]methyl]-4,4-dimethyl-3-isoxaolidinone as a yellow solid

Sources & evidence

ORD record
ord-748fbf33dd9a453cbb4af5f9a79620c7
Source dataset
uspto-grants-1987_09
Patent number
US04692182

Reaction notes

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