Thionyl Chloride → HCID 20261653, compound

HRID 465048Notes

Reaction equation

HRID 465048 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[NH:6][C:7]2[CH:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][C:8]=2[N:9]=1)[CH3:3].[S:16](Cl)(Cl)=O.S[CH:21]([CH3:24])[C:22]#[N:23].[Na].[O-]CC.[Na+]>CO>[C:22]([CH2:21][CH2:24][S:16][CH2:14][C:12]1[CH:11]=[CH:10][C:8]2[N:9]=[C:5]([CH2:4][N:2]([CH3:3])[CH3:1])[NH:6][C:7]=2[CH:13]=1)#[N:23]

Participants

7

Reactant 5

HCID 24386Thionyl ChlorideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 13600722HCID 13600722, compoundHCID 20261709HCID 20261709, compound

Product 1

HCID 20261653HCID 20261653, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Chloromethyl-2-dimethylaminomethylbenzimidazole, 2hydrochloride (melting point 248.4° C., 3.64 g) was produced by subjecting 2-dimethylaminomethyl-5-hydroxymethylbenzimidazole (3 g) and thionylchloride (10.5 ml) to a 4-hour refluxing with heat. 2-Mercaptopropionitrile (1.05 g) was changed into sodium salt by sodium ethoxide and, at a temperature of 0° C., methanol solution of the above-mentioned chloromethyl compound was added gradually and the mixture was stirred through one whole night at the room temperature to yield 5-[(2-cyanoethyl)thiomethyl]-2-dimethylaminomethylbenzimidazole (3.2 g).

Workup

  1. customto a 4-hour
  2. temperaturerefluxing
  3. temperaturewith heat
  4. additionwas added gradually

Sources & evidence

ORD record
ord-0f2febcda39844b08827069bbb96b160
Source dataset
uspto-grants-1985_10
Patent number
US04550118

Reaction notes

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