Ammonium Chloride → HCID 178431197, compound

HRID 367319Notes

Reaction equation

HRID 367319 reaction equation
C([O:4][C:5]1[C:6]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:7][C:8]2[O:12][C:11]([CH2:14][O:15][C:16]3[CH:27]=[CH:26][C:19]([CH:20]=[N:21][NH:22][C:23]([NH2:25])=[NH:24])=[CH:18][CH:17]=3)([CH3:13])[CH2:10][C:9]=2[C:28]=1[C:29]([CH3:32])([CH3:31])[CH3:30])(=O)C.C([Li])CCC.[Cl-].[NH4+]>O1CCCC1>[C:29]([C:28]1[C:9]2[CH2:10][C:11]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([CH:20]=[N:21][NH:22][C:23]([NH2:25])=[NH:24])=[CH:26][CH:27]=3)([CH3:13])[O:12][C:8]=2[CH:7]=[C:6]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:5]=1[OH:4])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178475395HCID 178475395, compound

Product 1

HCID 178431197HCID 178431197, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 2.0 g of 1-{4-[(5-acetoxy-4,6-di-t-butyl-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]benzylideneamino}guanidine was dissolved in 100 ml of tetrahydrofuran, and 10 ml of n-butyl lithium (1.6 M in n-hexane) was added and the mixture was stirred at room temperature for 30 minutes. After reaction, the reaction solution was combined with a saturated aqueous ammonium chloride solution and extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography eluting with chloroform containing 10% methanol to give 0.46 g of 1-{4-[(4,6-di-t-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran-2-yl)methoxy]benzylideneamino}guanidine as a pale yellow solid (yield 25%).

Workup

  1. customAfter reaction
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel column chromatography
  7. washeluting with chloroform containing 10% methanol

Sources & evidence

ORD record
ord-502e1f88ca0a4ec5a6c4c26b2e52a258
Source dataset
uspto-grants-2000_10
Patent number
US06133279

Reaction notes

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