Toluene → HCID 57437089, compound

HRID 1868219Notes

Reaction equation

HRID 1868219 reaction equation
C[C:2]1[N:3]=CNC=1.S(OCCC1C=CC=CC=1NC([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O)(C)(=O)=[O:8].ClCCl.[C:31]1([CH3:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[NH4+:3].[OH-:8].[C:24]([O:23][N:3]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:37][CH2:2]1)([CH3:25])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 10495550HCID 10495550, compoundHCID 178418800HCID 178418800, compound

Product 2

HCID 14923Ammonium HydroxideHCID 57437089HCID 57437089, compoundYield 22%

Procedure

4-Methylimidazole (6.7 g, 81.5 mmoles) and 2-(mesyloxy)-1-[2-[(tert-butoxycarbonyl)amino]phenyl]ethane (23.37 g, 74.1 mmoles) (Ref.:D. Critch and X. Hao, J. Org. Chem., 62, 1997, 5982-5988) were dissolved in anhydrous toluene (250 mL) and anhydrous dichloromethane (50 mL) and the mixture was heated under an argon atmosphere at 80° C. for 30 h. and then allowed to stand at 25° C. for 41 h. The solution was evaporated to dryness and the residue was chromatographed on silica gel using dichloromethane, then 3% (conc. NH4OH in methanol)-dichloromethane as the eluant to give N-tert-butoxyindoline (2.82 g, 22%) (Ref.: I. Masatomo and K. Tsukasa, Heterocycles, 34(5), 1992, 1031-1038) and the title mixture of imidazole compounds (4-Methyl:5-Methyl::66%:34%) (3.88 g, 34%).

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f50dad5cdeff4856ba2bfea63ed52485
Source dataset
uspto-grants-2009_12
Patent number
US07635697B2

Reaction notes

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