Water → 1-(2-Thienylmethyl)-1H-benzimidazole

HRID 2231248Notes

Reaction equation

HRID 2231248 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[H-].[Na+].Cl[CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1.O>CN(C)C=O>[S:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH2:13][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 5798BenzimidazoleHCID 24758Sodium hydrideHCID 698302-(Chloromethyl)thiophene

Product 1

HCID 212862851-(2-Thienylmethyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 11.81 g of benzimidazole in 50 ml of dimethylformamide was added 4.8 g of 50% sodium hydride in oil over 30 minutes. After stirring 30 minutes, 13.25 g of 2-chloromethylthiophene was added over a period of 30 minutes, and the reaction mixture stirred at room temperature overnight. The mixture was poured into water and the pH adjusted to 1.5. After extracting with ether, the pH was raised to 11 and precipitated product was filtered and dried, 19.9 g.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. extractionAfter extracting with ether
  3. temperaturethe pH was raised to 11
  4. customprecipitated product
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-2040f77ed6bd4cd185401eb348532417
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

Loading…