Oxalyl chloride → HCID 18505311, compound

HRID 1357267Notes

Reaction equation

HRID 1357267 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH2:7]([C:11]1[N:12]([CH3:23])[C:13]2[C:18](C=1C(O)=O)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH3:10]>C(Cl)Cl>[CH2:7]([C:11]1[N:12]([CH3:23])[C:13]2[C:14]([C:1]=1[C:2]([Cl:4])=[O:3])=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 18505279HCID 18505279, compound

Product 1

HCID 18505311HCID 18505311, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (5.89 mL, 66.1 mmol) was added under nitrogen to a solution of 2-butyl-1-methyl-1H-indole-3-carboxylic acid (3.06 g, 13.2 mmol), prepared in the previous step, in 100 mL of methylene chloride at room temperature. There was an immediate evolution of gas. After the addition the reaction was stirred at room temperature for 2 h. The solvent was removed under reduced pressure. To remove excess oxalyl chloride the residue was dissolved in benzene and the solvent removed under reduced pressure to give 2-butyl-1-methyl-1H-indole-3-carbonyl chloride as a brown oil. The material was immediately used without additional purification.

Workup

  1. additionAfter the addition the reaction
  2. customThe solvent was removed under reduced pressure
  3. customTo remove excess oxalyl chloride the residue
  4. dissolutionwas dissolved in benzene
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-31d5ba508d964e8a85336d9badc4db67
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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