Dimethyl Sulfoxide → HCID 12359654, compound

HRID 1016441Notes

Reaction equation

HRID 1016441 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH3:28])[CH2:13][CH2:14][C:15]1[N:19]([CH2:20][CH2:21][C:22]#[N:23])[C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=2[N:16]=1.C(N(CC)CC)C>C(Cl)Cl.O>[O:11]=[C:12]([CH3:28])[CH2:13][CH2:14][C:15]1[N:19]([CH2:20][CH2:21][C:22]#[N:23])[C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=2[N:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18407009HCID 18407009, compound

Product 1

HCID 12359654HCID 12359654, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1.0 mL of oxalyl chloride in 30 mL of methylene chloride cooled to −78° C. was added 2 mL of anhydrous DMSO. After 10 min, a solution of 2.1 g of 3-[2-(3-hydroxy-butyl)-benzimidazol-1-yl]-propionitrile in 150 mL of dichloromethane was added keeping the temperature below −50° C. After 10 min, 10 mL of triethyl amine was added and the mixture allowed to warm to room temperature. After 15 min, the mixture was diluted with 250 mL of water, shaken and separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum gave 2.2 g of 3-[2-(3-oxo-butyl)-benzimidazol-1-yl]-propionitrile as an amber resin.

Workup

  1. customthe temperature below −50° C
  2. waitAfter 10 min
  3. waitAfter 15 min
  4. customseparated
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customDrying under vacuum

Sources & evidence

ORD record
ord-72898ce85bd9444ba9c81ba864dad817
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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