Triethylamine → HCID 18407014, compound

HRID 1016438Notes

Reaction equation

HRID 1016438 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][CH2:9][CH:10]([C:12]1[N:16]([CH2:17][CH2:18][C:19]#[N:20])[C:15]2[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=2[N:13]=1)[CH3:11].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O.O>[CH3:11][CH:10]([C:12]1[N:16]([CH2:17][CH2:18][C:19]#[N:20])[C:15]2[CH:21]=[CH:22][CH:23]=[CH:24][C:14]=2[N:13]=1)[CH2:9][CH:8]=[O:7]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 184070112-(3-Hydroxy-1-methylpropyl)-1H-benzimidazole-1-propanenitrile

Product 1

HCID 18407014HCID 18407014, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1.0 mL of oxalyl chloride in 20 mL of methylene chloride cooled to −78° C. was added 2 mL of anhydrous DMSO. After 15 min, a solution of 1 g of 3-[2-(3-hydroxy-1-methyl-propyl)-benzoimidazol-1-yl]-propionitrile in 20 mL of anhydrous DMSO and 50 mL of methylene chloride 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. The crude 3-[2-(3-oxo-propyl)-benzimidazol-1-yl]-propionitrile was an amber resin (1.2 g), and contained only traces of the starting alcohol by TLC (90:10 methylene chloride:methanol).

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

Sources & evidence

ORD record
ord-9c76946f02ef4cfdac386d63835d4374
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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