Trityl chloride → HCID 67204988, compound

HRID 1023882Notes

Reaction equation

HRID 1023882 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]2[NH:20][CH:19]=[N:18][CH:17]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]2[N:20]=[CH:19][N:18]([C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:17]=2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 67206963HCID 67206963, compound

Product 1

HCID 67204988HCID 67204988, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(benzyloxy)-2-(1H-imidazol-5-yl)phenol (0.488 mmol) in DMF (5 mL) was added triethylamine (0.585 mmol). After stirring for 10 min, chlorotriphenylmethane (0.512 mmol) was added and continued stirring for 16 h. The reaction mixture was diluted with water (25 mL) and the precipitated product was filtered and washed with water (3×10 mL). The solid cake was dissolved in CH2Cl2, washed with water, brine and dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. The crude was purified by column chromatography to afford the final product (0.230 g, 47%).

Workup

  1. stirringcontinued stirring for 16 h
  2. filtrationthe precipitated product was filtered
  3. washwashed with water (3×10 mL)
  4. dissolutionThe solid cake was dissolved in CH2Cl2
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product
  9. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-c0b675d867e044388f24c61ba28b7903
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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