Oxalyl chloride → 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonyl chloride

HRID 23419Notes

Reaction equation

HRID 23419 reaction equation
Cl.[NH:2]1[CH2:6][CH2:5][N:4]=[C:3]1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([OH:20])(=O)=[O:18])=[CH:9]1.C(Cl)(=O)C([Cl:24])=O>C(Cl)Cl>[NH:2]1[CH2:6][CH2:5][N:4]=[C:3]1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([Cl:24])(=[O:20])=[O:18])=[CH:9]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 865902821-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic acid hydrochloride

Product 1

HCID 225740201-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonic acid hydrochloride (1.52 g, 4.814 mmol) from Step 3 was dissolved/suspended in methylene chloride (25 mL) and stirred at room temperature. Oxalyl chloride (2 mL) was added dropwise to the mixture, after which stirring was continued for 3 hours. The mixture was then evaporated to dryness, and excess oxyalyl chloride was azeotroped off with methylene chloride (3×) to provide 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-1H-indole-3-sulfonyl chloride as a hydrochloride salt.

Workup

  1. stirringafter which stirring
  2. customThe mixture was then evaporated to dryness, and excess oxyalyl chloride
  3. customwas azeotroped off with methylene chloride (3×)

Sources & evidence

ORD record
ord-4c45fcacefb442dab2cb34acbfc66df6
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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