Ammonium Chloride → HCID 21928206, compound

HRID 749203Notes

Reaction equation

HRID 749203 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]2[C:9]([CH3:12])=[N:10][O:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[Li+].CC([N-]C(C)C)C.I[CH2:24][C:25]1[N:26]=[C:27]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])[O:28][C:29]=1[CH:30]([CH3:32])[CH3:31].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]2[C:9]([CH2:12][CH2:24][C:25]3[N:26]=[C:27]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=4[Cl:40])[O:28][C:29]=3[CH:30]([CH3:32])[CH3:31])=[N:10][O:11][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 10241934HCID 10241934, compoundHCID 12993427HCID 12993427, compound

Product 1

HCID 21928206HCID 21928206, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

6-Acetamido-3-methyl-1,2-benzisoxazole (571 mg, 3.00 mmol) was dissolved in dry THF (18 mL). 2M of LDA (3.1 mL, 6.2 mmol) was dropwise added to the solution for 10 minutes under nitrogen atmosphere at −78° C. A solution of 4-iodomethyl-5-isopropyl-2-(2,4-dichlorophenyl)oxazole (1.19 g, 3.00 mmol) in THF (3.0 mL) was dropwise added to the resulting mixture for 7 minutes. The mixture was stirred for 1 hour under the same conditions. The mixture was allowed to room temperature. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the mixture. The organic layer was washed with water and saline, and dried over anhydrous sodium sulfate. Ethyl acetate was removed under reduced pressure. The residue was purified by column chromatography on silica gel with chloroform/methanol (80/1) to give the desired compound (904 mg) as pale yellow oil (yield 70%).

Workup

  1. customwas allowed to room temperature
  2. washThe organic layer was washed with water and saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEthyl acetate was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel with chloroform/methanol (80/1)

Sources & evidence

ORD record
ord-71b09e1ff7d544fcaf40f6b78bc530c5
Source dataset
uspto-grants-2008_07
Patent number
US07402597B2

Reaction notes

Loading…