1-Propanol → HCID 20392015, compound

HRID 1863515Notes

Reaction equation

HRID 1863515 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)=[CH:3][CH:2]=1.[CH2:16]([Cl:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)CC>CS(C)=O>[Cl-:23].[O:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[C:7]1[C:4]1[CH:3]=[CH:2][N+:1]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 7503Benzyl ChlorideHCID 16804Benzoxazole, 2-(4-pyridyl)-

Product 1

HCID 20392015HCID 20392015, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 117.0 g of 2-(4-pyridinyl)benzoxazole and 95.0 g of benzyl chloride in 1 liter of a 9:1 mixture of n-propanol and dimethylsulfoxide is heated at reflux for 72 hours. The solvent mixture is then removed and the residue suspended in 100 ml of water. The crystalline product which separates is filtered, washed with acetone, and dried to give 76.6 g of product. Concentration of the mother liquors gives an additional 27.8 g of product, melting point 194°-196° C., dec. Recrystallization from water and drying in a vacuum at 100° C. for 5 hours raises the melting point to 216°-217° C., dec.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 72 hours
  3. customThe solvent mixture is then removed
  4. filtrationThe crystalline product which separates is filtered
  5. washwashed with acetone
  6. customdried

Sources & evidence

ORD record
ord-da1674f54c5a4d268df960aeb12ebab5
Source dataset
uspto-grants-1979_09
Patent number
US04169200

Reaction notes

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