Triethylamine → HCID 18973252, compound

HRID 2394398Notes

Reaction equation

HRID 2394398 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][N:7]2[CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18].C(N(CC)CC)C.[Cl-].[NH4+]>CS(C)=O>[CH3:18][C:17]1[O:16][C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:14][C:13]=1[CH2:12][N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:3]([CH:2]=[O:1])[C:4]=2[CH:5]=[CH:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 18973255HCID 18973255, compound

Product 1

HCID 18973252HCID 18973252, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

There were dissolved, in 14 ml of dimethylsulfoxide, 700 mg of 4-hydroxymethyl-1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole prepared in Example 29 and 890 mg of triethylamine, followed by addition of 700 mg of sulfur trioxide-pyridine complex to the solution and stirring for 30 minutes. The reaction solution was added to 100 ml of a 10% ammonium chloride aqueous solution, followed by extraction with ethyl acetate (50 ml×3). The resulting organic phase was washed, in turn, with water (50 ml×2) and 50 ml of a saturated common salt solution and dried over anhydrous sodium sulfate. After removal of the solvent through distillation under reduced pressure, the resulting residue was crystallized in 50 ml of ether to thus give 640 mg of 1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 84%.

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  2. washThe resulting organic phase was washed, in turn, with water (50 ml×2) and 50 ml of a saturated common salt solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter removal of the solvent
  5. distillationthrough distillation under reduced pressure
  6. customthe resulting residue was crystallized in 50 ml of ether to thus give 640 mg of 1-[(5-methyl-2-phenyloxazol-4-yl)methyl]indole-4-carbaldehyde as pale yellow crystals
  7. customThe yield

Sources & evidence

ORD record
ord-9d15f7af76cd41f9a67f5fdf662bb56b
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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