Imidazole → 4-(Tert-butyldimethylsilyl)oxy-2-nitroaniline

HRID 1264069Notes

Reaction equation

HRID 1264069 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1.CN(C=O)C>CCOCC>[CH3:13][Si:12]([CH3:14])([C:15]([CH3:18])([CH3:17])[CH3:16])[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 120422994-(Tert-butyldimethylsilyl)oxy-2-nitroanilineYield 76.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 4-amino-3-nitrophenol (20 g, 128.9 mmol) was added tert-butyldimethylsilyl chloride (21.5 g, 142.9 mmol), imidazole (13.3 g, 194.8 mmol), and DMF (100 mL). The mixture was stirred at room temperature for 3 h and then diluted with Et2O and washed with H2O. The organics were concentrated under reduced pressure and the resulting solid recrystallized from Et2O—H2O; yielding 26.5 g (76%) product.

Workup

  1. washwashed with H2O
  2. concentrationThe organics were concentrated under reduced pressure
  3. customthe resulting solid recrystallized from Et2O—H2O

Sources & evidence

ORD record
ord-742240df46644f58a7392ea11dd80618
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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