Water → 2-Methyl-1-tritylimidazole

HRID 1498062Notes

Reaction equation

HRID 1498062 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.O>CN(C)C=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 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 127492-Methylimidazole

Product 1

HCID 6182462-Methyl-1-tritylimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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) in 20 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-6964135d4de444fbae6b9f2bf13f4f19
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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