Dimethylformamide → 2-Methyl-1-tritylimidazole

HRID 1629032Notes

Reaction equation

HRID 1629032 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(N(CC)CC)C.CN(C)C=O>O>[CH3:21][C:22]1[N:23]([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:24]=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 127492-Methylimidazole

Product 1

HCID 6182462-Methyl-1-tritylimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triphenylmethyl chloride (16.0 g, 57.5 mmol) was added portionwise to a solution of 2-methylimidazole (4.10 g, 50.0 mmol) and Triethylamine (9.02 mL, 64.7 mmol) in20 ml of N,N-dimethylformamide. The mixture was stirred for 18 hours, mixed with 300 ml of water and extracted with 1000 ml of ethyl acetate. The organic extract was washed with 1 L of water, brine, dried over MgSO4 and concentrate in vacuum to 50 ml volume. A precipitate was collected, washed with ethyl acetate and dried in high vacuum for 18 hours. Weight 15.0 g (92.5%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.29 (m, 9H), 7.16-7.11 (m, 6H), 6.90 (d, J=1.5, 1H), 6.71 (d, J=1.5, 1H), 1.65 (s, 3H).

Workup

  1. extractionextracted with 1000 ml of ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with 1 L of water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrate in vacuum to 50 ml volume
  6. customA precipitate was collected
  7. washwashed with ethyl acetate
  8. customdried in high vacuum for 18 hours

Sources & evidence

ORD record
ord-de00323ecde94ad8b064dfbad43153bb
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

Loading…