Imidazole → HCID 67397341, compound

HRID 1526408Notes

Reaction equation

HRID 1526408 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].N1C=CN=C1.[CH:15]([Si:18](Cl)([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16]>C1COCC1.CC(OC)(C)C>[CH3:9][C:3]1[CH:4]=[C:5]([O:8][Si:18]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:15]([CH3:17])[CH3:16])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 178194-Amino-m-cresolHCID 139400Triisopropylsilyl chloride

Product 1

HCID 67397341HCID 67397341, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-amino-3-methylphenol (75.0 g, 609 mmol) in THF (1.5 L) was added imidazole (83 g, 1.22 mol). The reaction was cooled to 0° C. and triisopropylsilyl chloride (123 mL, 579 mmol) was added. The reaction mixture was allowed to warm to room temperature, stirred for 3 h, diluted with MTBE (1.5 L) and filtered. The filtrate was washed with water (1.0 L). The aqueous phase was back-extracted with MTBE (500 mL). The organics were combined, washed with 0.5 N NaOH (2×500 mL), brine (500 mL), and dried over MgSO4. The organics were filtered and concentrated to give 2-methyl-4-(triisopropylsilyloxy)aniline (135 g, 482 mmol, 83% yield) as a red oil. Exact mass calculated for C16H29NOSi: 279.2, found: LCMS m/z=280.5, [M+H+]; 1H NMR (400 MHz, CDCl3) δ ppm 1.09 (d, J=7.0 Hz, 18 H), 1.21 (m, 3 H), 2.12 (s, 3 H), 3.31 (bs, 2 H), 6.53 (d, J=8.4 Hz, 1 H), 6.57 (dd, J1=8.4, J2=2.7 Hz, 1 H), 6.62 (d, J=2.7 Hz, 1 H).

Workup

  1. temperatureto warm to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water (1.0 L)
  4. extractionThe aqueous phase was back-extracted with MTBE (500 mL)
  5. washwashed with 0.5 N NaOH (2×500 mL), brine (500 mL)
  6. dry with materialdried over MgSO4
  7. filtrationThe organics were filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0739c523ccb44658a314c5a0a8086544
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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