Ammonium Chloride → HCID 20088788, compound

HRID 275535Notes

Reaction equation

HRID 275535 reaction equation
C([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([CH:15]([NH:17][OH:18])[CH3:16])=[CH:7][C:6]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=O)C.C[Si]([N:27]=[C:28]=[O:29])(C)C.[NH4+].[Cl-]>C1COCC1>[CH3:12][C:11]([C:10]1[CH:9]=[C:8]([CH:15]([N:17]([OH:18])[C:28]([NH2:27])=[O:29])[CH3:16])[CH:7]=[C:6]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:5]=1[OH:4])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanateHCID 54086794HCID 54086794, compound

Product 1

HCID 20088788HCID 20088788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.814 g (0.0025 mole) of 2,6-bis (1,1-dimethylethyl) -4- [1- (hydroxyamino)ethyl]phenol acetate (Example 2) in THF (10 mL) is added 0.868 g (0.0075 mole) of 85% trimethylsilyl isocyanate. The reaction mixture is heated under reflux for 45 minutes and allowed to stand at room temperature for 16 hours. The mixture is poured into saturated NH4Cl, concentrated to remove THF, extracted with EtOAc and dried over Na2SO4. The extracts are evaporated to dryness and the residue is recrystallized from Et2O-n-hexane to give white crystals, 0.46 g (60%), m.p. 162°-163.5° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 45 minutes
  3. concentrationconcentrated
  4. customto remove THF
  5. extractionextracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. customThe extracts are evaporated to dryness
  8. customthe residue is recrystallized from Et2O-n-hexane
  9. customto give white crystals, 0.46 g (60%), m.p. 162°-163.5° C.

Sources & evidence

ORD record
ord-97ed4d4ff7d042f8b4d7d81294c09bc1
Source dataset
uspto-grants-1995_02
Patent number
US05393923

Reaction notes

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