Triethylamine → HCID 12017139, compound

HRID 2303335Notes

Reaction equation

HRID 2303335 reaction equation
C(Cl)(=O)C(Cl)=O.[OH:7][CH2:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][C:18]#[N:19])[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=2[N:12]=1.C(N(CC)CC)C>C(Cl)Cl.CS(C)=O.O>[O:7]=[CH:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][C:18]#[N:19])[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=2[N:12]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 12017138HCID 12017138, compound

Product 1

HCID 12017139HCID 12017139, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 0.5 g of oxalyl chloride in 15 mL of methylene chloride cooled to −78° C. was added 1 mL of anhydrous DMSO. After 15 min, a solution of 1 g of 3-[2-(3-hydroxy-propyl)-benzimidazol-1-yl]-propionitrile in 50 mL of methylene chloride and 10 mL of anhydrous DMSO was added while keeping the temperature below −50° C. There was considerable precipitate which redissolved on warming to 0° C. over 20 min. After cooling back down to −50° C., 5 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 g), and contained only traces of the starting alcohol by TLC (90:10 methylene chloride:methanol).

Workup

  1. customthe temperature below −50° C
  2. dissolutionredissolved
  3. temperatureAfter cooling back down to −50° C.
  4. temperatureto warm to room temperature
  5. waitAfter 15 min
  6. customseparated
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b23f2f57c75b41d886e25521aadef87c
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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