Imidazole → HCID 58438184, compound

HRID 2092377Notes

Reaction equation

HRID 2092377 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].N1C=CN=C1.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C=O)C>[C:16]([Si:19]([CH3:21])([CH3:20])[O:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[NH2:1])([CH3:18])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 760822-Amino-5-methylphenol

Product 1

HCID 58438184HCID 58438184, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-5-methyl-phenol (500 mg, 4.0 mmol) and imidazole (298 mg, 4.4 mmol) in DMF (5 ml) was added TBDMSCl (660 mg, 4.4 mmol). The reaction mixture was stirred at RT for 3 h then diluted into water and extracted with AcOEt. The organic fraction was dried over Na2SO4, filtered and evaporated to dryness. The resulting residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME containing 5% of 7M NH3 in MeOH 95:5→8:2) to yield the title compound (724 mg, 3.1 mmol, 77%) as a redish oil. TLC: RF=0.94 (heptane/DCM/TBME 1:1:2 containing 5% of 7M NH3 in MeOH); HPLC: AtRet=1.80 min; API-MS: m/z 238.1 [M+H]+; 1H NMR (400 MHz, CDCl3): 0.26 (s, 6H), 1.04 (s, 9H), 2.23 (s, 3H), 3.56 (br. s., 1H), 6.56-6.67 (m, 3H).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, heptane/TBME containing 5% of 7M NH3 in MeOH 95:5→8:2)

Sources & evidence

ORD record
ord-256928d8d0fe40bc8cdfe016282b73fb
Source dataset
uspto-grants-2013_05
Patent number
US08440693B2

Reaction notes

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