Triethylamine → 2,3-Dihydro-1H-indole-1-carbonyl chloride

HRID 413280Notes

Reaction equation

HRID 413280 reaction equation
[O:1]=[C:2]([Cl:8])OC(Cl)(Cl)Cl.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.C(N(CC)CC)C>ClCCl>[N:9]1([C:2]([Cl:8])=[O:1])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10328IndolineHCID 10426Diphosgene

Product 1

HCID 223907682,3-Dihydro-1H-indole-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

22.5 mmol of diphosgene dissolved in 90 ml of dichloromethane are cooled to 0° C.; there are then added 45 mmol of indoline, and then 67.5 mmol of triethylamine, while maintaining the temperature at 0° C. After 12 hours at ambient temperature, the mixture is filtered and the filtrate is concentrated under reduced pressure.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-49f283c9049b4e099089e5b70fd093ca
Source dataset
uspto-grants-2003_05
Patent number
US06566364B2

Reaction notes

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