Dichloromethane → 4-Methyl-2'-(2-oxo-3-trityl-1,3,4-oxadiazol-5-yl)biphenyl

HRID 326228Notes

Reaction equation

HRID 326228 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[O:18][C:17](=[O:19])[NH:16][N:15]=2)=[CH:4][CH:3]=1.[C:20](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)Cl>C(N(CC)CC)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[O:18][C:17](=[O:19])[N:16]([C:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:15]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 186931434-Methyl-2'-(2-oxo-1,3,4-oxadiazol-5-yl)biphenyl

Product 1

HCID 186930024-Methyl-2'-(2-oxo-3-trityl-1,3,4-oxadiazol-5-yl)biphenyl

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2.03 g of the compound prepared in step B, 2.5 g of trityl chloride, 50 ml of DCM and 1.6 ml of triethylamine are placed in a round-bottomed flask and the mixture is refluxed for 1 and a half hours. It is evaporated, the residue is taken up with an ethyl ether/water mixture and the organic phase is washed with a 3% solution of potassium hydrogensulfate, dried over sodium sulfate, filtered and evaporated. The product is used in the crude form for the next step.

Workup

  1. temperaturethe mixture is refluxed for 1 and a half hours
  2. customIt is evaporated
  3. washthe organic phase is washed with a 3% solution of potassium hydrogensulfate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-11a19c9aa91a40d48a6b8760f8afed25
Source dataset
uspto-grants-1993_12
Patent number
US05268375

Reaction notes

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