Imidazole → HCID 597274, compound

HRID 326796Notes

Reaction equation

HRID 326796 reaction equation
N1C=CN=C1.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].Cl[Si:15]([CH3:18])([CH3:17])[CH3:16].CCOCC>CN(C)C=O.CCCCCC>[CH3:16][Si:15]([CH3:18])([CH3:17])[O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[NH2:6]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 58012-AminophenolHCID 6397Chlorotrimethylsilane

Product 1

HCID 597274HCID 597274, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

Imidazole (3.73 g) was added in one portion to a solution of 2-aminophenol (2.0 g) in dry dimethylformamide (10 ml) stirred at 25° C. under nitrogen. Chlorotrimethylsilane (2.98 g) was added dropwise over 5 minutes and stirring continued for a further 18 hours. The mixture was poured onto water (30 ml) and extracted with diethyl ether (2×60 ml). The organic solution was separated and washed with 2N sodium hydroxide (2×40 ml), brine and dried over magnesium sulphate. Evaporation of the filtrate under reduced pressure gave an oil. Column chromatography on silica eluting with 10% ether:hexane gave 2-trimethylsilyloxyaniline (0.85 g). NMR 1H: 0.2(9H,s), 3.5(2H,s), 6.4(4H,m).

Workup

  1. stirringstirring
  2. additionThe mixture was poured onto water (30 ml)
  3. extractionextracted with diethyl ether (2×60 ml)
  4. customThe organic solution was separated
  5. washwashed with 2N sodium hydroxide (2×40 ml), brine
  6. dry with materialdried over magnesium sulphate
  7. customEvaporation of the filtrate under reduced pressure
  8. customgave an oil

Sources & evidence

ORD record
ord-e89549487d0247258136738622933b28
Source dataset
uspto-grants-1993_12
Patent number
US05270343

Reaction notes

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