2-Aminophenol → HCID 23366240, compound

HRID 1080900Notes

Reaction equation

HRID 1080900 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(CC)CC)C.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].[C:24](Cl)(Cl)=[O:25]>O1CCCC1.C1(C)C=CC=CC=1>[Si:16]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:1]=[C:24]=[O:25])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 6371PhosgeneHCID 8471Triethylamine2×HCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 23366240HCID 23366240, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 g (9.16 mmol) of o-aminophenol in 10 mL of tetrahydrofuran was added 3.57 mL (2.59 g; 25.6 mmol) of triethylamine and 3.46 g (22.9 mmol) of t-butyldimethylsilyl chloride. The reaction mixture was stirred for 15 hours at room temperature, filtered and concentrated in vacuo. The residue was dissolved in 10 mL of toluene and this solution was cooled to -15° C. The solution was treated with 1.4 mL (1.02 g; 10.0 mmol) of triethylamine, followed by the dropwise addition of 4.75 mL (9.17 mmol) of a 1.93M solution of phosgene in toluene. After the addition was complete, the reaction mixture was allowed to warm up to room temperature and stirred at that temperature for 1 hour. The mixture was filtered and the filtrate was concentrated in vacuo to give a pink oil. IR (neat) 2251 cm-1 ; 1H NMR (CDCl3) δ7.060 (dt, J=8.4, 2.0 Hz, 1H, ArH), 7.018 (dd, J=7.6, 2.0 Hz, 1H, ArH), 6.950-6.850 (m, with d at 6.894, J=7.6 Hz, 2H, ArH), 1.08 (s, 9H, CCH3), 0.350 (s, 6H, SiCH3); MS (EI) m/z=192 (100%), 249 (M+).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 10 mL of toluene
  4. temperaturethis solution was cooled to -15° C
  5. additionAfter the addition
  6. temperatureto warm up to room temperature
  7. stirringstirred at that temperature for 1 hour
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customto give a pink oil

Sources & evidence

ORD record
ord-675f958d8b9542ff8f336eeca345e520
Source dataset
uspto-grants-1996_12
Patent number
US05583235

Reaction notes

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