Thionyl Chloride → HCID 18677034, compound

HRID 1634019Notes

Reaction equation

HRID 1634019 reaction equation
O[CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=2[N:4]=1.S(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:19][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH2:10][C:11]#[N:12])[C:6]2[CH:13]=[CH:14][CH:15]=[CH:16][C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 225957974-(2-Hydroxymethyl-benzoimidazol-1-yl)-butyronitrile

Product 1

HCID 18677034HCID 18677034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(2-hydroxymethyl-benzoimidazol-1-yl)-butyronitrile, 68, (22 g, 102.2 mmol) suspended in CH2Cl2 (100 mL), thionyl chloride (15.81 g, 132.9 mmol) was slowly added with ice-water bath cooling. The ice bath was removed. The solution was stirred at room temperature for 1 hour and then evaporated. The residue was triturated with EtOAc to give a nearly quantitative yield of 4-(2-chloromethyl-benzoimidazol-1-yl)-butyronitrile, 69, as light gray powder.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. customevaporated
  4. customThe residue was triturated with EtOAc

Sources & evidence

ORD record
ord-faa6ac9776844d6995ce0d2e019a03fd
Source dataset
uspto-grants-2003_01
Patent number
US06506738B1

Reaction notes

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