Ammonium Chloride → HCID 10156109, compound

HRID 413737Notes

Reaction equation

HRID 413737 reaction equation
[NH4+:1].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:7]([C:10]1[C:11]([O:26][C:27]([CH3:33])([CH3:32])[C:28](OC)=[O:29])=[C:12]([CH2:23][CH2:24][CH3:25])[C:13]2[O:17][N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[C:14]=2[CH:22]=1)[CH2:8][CH3:9]>C1(C)C=CC=CC=1>[CH2:7]([C:10]1[C:11]([O:26][C:27]([CH3:33])([CH3:32])[C:28]([NH2:1])=[O:29])=[C:12]([CH2:23][CH2:24][CH3:25])[C:13]2[O:17][N:16]=[C:15]([C:18]([F:21])([F:20])[F:19])[C:14]=2[CH:22]=1)[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 9930125HCID 9930125, compound

Product 1

HCID 10156109HCID 10156109, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of NH4Cl (86 mg) in toluene (10 mL) at room temperature was added AlCl3 (2.0 M, 0.8 mL) dropwise. The reaction was stirred for 3 h. The resultant clear solution was transferred to a solution of methyl 2-[(5,7-dipropyl-3-trifluoromethyl-1,2-benzisoxazol-6-yl)oxy]-2-methylpropionate (200 mg) in toluene (5 mL). The reaction was stirred at 80° C. overnight, cooled to room temperature, and then partitioned between EtOAc and 1.0 N aqueous HCl solution. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by chromatography gave the desired product. 1H NMR (CDCl3) δ 1.00 (m, 6H), 1.51 (s, 6H), 1.65 (m, 2H), 1.75 (m, 2H), 2.70 (t, 2H), 2.94 (m, 2H), 5.72 (s, broad, 1H), 6.87 (s, broad, 1H), 7.43 (s, 1H).

Workup

  1. stirringThe reaction was stirred at 80° C. overnight
  2. custompartitioned between EtOAc and 1.0 N aqueous HCl solution
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-88a8314e7985414ca4f4508f638c7b42
Source dataset
uspto-grants-2003_05
Patent number
US06569879B2

Reaction notes

Loading…