HCID 14923120, compound → HCID 14684983, compound

HRID 1064827Notes

Reaction equation

HRID 1064827 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2]>[C].[Pd].C(O)C>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:6]=1[OH:14]

Participants

4

Reactant 1

HCID 14923120HCID 14923120, compound

Product 1

HCID 14684983HCID 14684983, compoundYield 97.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A 10% palladium carbon catalyst (250 mg) was added to a solution of the nitrophenol (316 mg, 1.62 mmol) in ethanol (20 ml) and stirred under hydrogen atmosphere at room temperature for 12 hours. The reaction solution was filtered off through celite and the filtrate was evaporated in vacuo to provide 260 mg (yield 97%) of 2-amino-6-tert-butylphenol as red crystals. Potassium O-ethyl dithiocarbonate (242 mg, 1.51 mmol) was added to a solution of the aminophenol (227 mg, 1.37 mmol) in ethanol (10 ml) followed by heating to reflux for eight hours. After allowing to cool, the solvent was evaporated in vacuo and the resulting residue was dissolved in water, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over an hydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (20 g of silica gel; developing solvent, hexane:acetone=4:1) to provide 124 mg (yield 44%) of 7-tert-butyl-2-mercaptobenzooxazole as colorless crystals.

Workup

  1. filtrationThe reaction solution was filtered off through celite
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-1bc4f6ecc4d048bfbe4075855ae627b0
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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