2-(1,2-Dibromoethyl)pyridine hydrobromide → 7-Ethoxy-2,3-dihydro-2-(2-pyridyl)thiazolo[3,2-a]benzimidazole

HRID 2351293Notes

Reaction equation

HRID 2351293 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]=[C:9]([SH:11])[NH:10][C:6]=2[CH:5]=1)[CH3:2].CC(C)([O-])C.[K+].Br.Br[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH2:23]Br>CC(O)(C)C>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:7]2[N:8]3[CH2:23][CH:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[S:11][C:9]3=[N:10][C:6]=2[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 198460922-(1,2-Dibromoethyl)pyridine hydrobromideHCID 23665647Potassium tert-butoxideHCID 178466039HCID 178466039, compound

Product 1

HCID 198460997-Ethoxy-2,3-dihydro-2-(2-pyridyl)thiazolo[3,2-a]benzimidazole

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

5-Ethoxy-2-mercaptobenzimidazole (6.03 g) was suspended in 2-methylpropan-2-ol (100 ml) at 50° C. Potassium tert-butoxide (3.48 g) was added and the mixture stirred for 1 hour. The temperature was allowed to fall to 35° C. and 2-(1,2-dibromoethyl)pyridine hydrobromide (10.76 g) was added. The resulting mixture was stirred for 1 hour at 35° C. and then 2 hours at reflux.

Workup

  1. customto fall to 35° C.
  2. stirringThe resulting mixture was stirred for 1 hour at 35° C.
  3. temperature2 hours at reflux

Sources & evidence

ORD record
ord-38f517fd53104a3ab0c865603b9537f6
Source dataset
uspto-grants-1989_10
Patent number
US04873237

Reaction notes

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