Imidazole → 2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-chloroaniline

HRID 272296Notes

Reaction equation

HRID 272296 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][OH:10].N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>O1CCCC1>[Si:20]([O:10][CH2:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[NH2:1])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 5867542-Amino-5-chlorobenzyl alcohol

Product 1

HCID 589931822-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-chloroaniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-amino-5-chlorophenylmethanol (11.1 g, 70.4 mmol) in tetrahydrofuran (50 mL) was added imidazole (5.27 g, 77.5 mmol), followed by careful addition of tert-butyldimethylchlorosilane (10.62 g 70.4 mmol). The reaction mixture was stirred for 24 hours. Imidazole (528 mg, 7.75 mmol) and tert-butyldimethylchlorosilane (1.06 g, 7.03 mmol) were then added. After 1 hour the solid was filtered off and washed with diethyl ether (2×20 mL) and the filtrate was washed with water (10 mL), brine (10 mL), dried over magnesium sulfate and concentrated in vacuo to give the product as a brown oil, 18.83 g (98%).

Workup

  1. filtrationAfter 1 hour the solid was filtered off
  2. washwashed with diethyl ether (2×20 mL)
  3. washthe filtrate was washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ab986cc614343b0a2f1168e87fea6ec
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

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