Potassium Hydroxide → HCID 19866738, compound

HRID 1199453Notes

Reaction equation

HRID 1199453 reaction equation
[SH:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.[OH-].[K+]>CN1CCCC1>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:13]1[CH:12]=[CH:17][CH:16]=[CH:15][C:14]=1[S:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 132239292-(2-Bromophenyl)pyridineHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 19866738HCID 19866738, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Procedure

2-Mercapto benzoxazole (604 mg; 4 mmole) was reacted with 2-(2-bromophenyl)pyridine (936 mg; 4 mmole) in the presence of KOH (224 mg; 4 mmole) in N-methyl pyrrolidine (16 ml). The mixture was heated under reflux for 6 hours, worked up and flash chromatographed (silica), using ethyl acetate/petroleum ether (2/3) eluant to give the sub-title compound as a pale brown oil (52 mg; 4.3%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customflash chromatographed (silica)

Sources & evidence

ORD record
ord-b8b8c4af65c849b8a26993cfb121935b
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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