Ammonium Chloride → HCID 66884043, compound

HRID 241381Notes

Reaction equation

HRID 241381 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:15])[C:9]([NH:11][C:12](=[O:14])[CH3:13])=[CH:10][C:5]=2[O:4][N:3]=1.[Li+].CC([N-]C(C)C)C.Cl[CH2:25][C:26]1[S:27][C:28]2[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:29]=2[C:30]=1[CH:31]([CH3:33])[CH3:32].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH:31]([C:30]1[C:29]2[CH:34]=[CH:35][C:36]([C:38]([F:41])([F:39])[F:40])=[CH:37][C:28]=2[S:27][C:26]=1[CH2:25][CH2:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:15])[C:9]([NH:11][C:12](=[O:14])[CH3:13])=[CH:10][C:5]=2[O:4][N:3]=1)([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 21928234N-(3,5-Dimethyl-1,2-benzoxazol-6-yl)acetamideHCID 66883686HCID 66883686, compound

Product 1

HCID 66884043HCID 66884043, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-(3,5-dimethylbenzisoxazol-6-yl)acetamide (381 mg, 1.87 mmol) in anhydrous THF (15 mL) was added dropwise 2M LDA (2.3 mL, 4.6 mmol) for 30 min at −78° C. under N2 atmosphere. The mixture was stirred for 30 min at −78° C., to which a solution of 2-chloromethyl-3-isopropyl-6-(trifluoromethyl)benzothiophene (655 mg, 2.24 mmol) in THF (5.0 mL) was added dropwise for 30 min. The mixture was stirred for 2 h at the same temperature, and then warmed to room temperature. A saturated aqueous ammonium chloride and ethyl acetate were added to the reaction mixture. The organic layer was washed with water, brine, and dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography (hexane/ethyl acetate, 1:1) to give the titled compound as a pale yellow crystal (426 mg, yield. 50%).

Workup

  1. additionwas added dropwise for 30 min
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter the solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-5f56bf0539084eab983e0a691b15359a
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

Loading…