Triethylamine → HCID 86652122, compound

HRID 2360012Notes

Reaction equation

HRID 2360012 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:14][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:15])=[CH:13][CH:12]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 86652122HCID 86652122, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl-4-hydroxyphenylcarbamate (1.0 g, 4.78 mmol) and triethylamine (0.80 mL, 5.73 mmol) were combined in dichloromethane (50 mL), cooled in an ice bath and treated with methanesulfonyl chloride (0.41 mL, 5.26 mmol). The solution was stirred at ambient temperature for 2 h, then was washed with 1M HCl, dried over sodium sulfate, filtered, and concentrated to give 1.2 g (87%).

Workup

  1. temperaturecooled in an ice bath
  2. washwas washed with 1M HCl
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give 1.2 g (87%)

Sources & evidence

ORD record
ord-4bdf13f5e3914757941f1c629ad41dd3
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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