Triethylamine → HCID 21460715, compound

HRID 2082524Notes

Reaction equation

HRID 2082524 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18](N(CC)CC)C.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29].C(OCC)(=O)C>C(Cl)Cl>[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](=[O:29])[CH2:18][NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=2[Cl:11])[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 98082-Fluorobenzoyl chlorideHCID 15043966HCID 15043966, compound

Product 1

HCID 21460715HCID 21460715, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (1.09 g, 4 mmol) in methylene chloride (25 mL) and add triethylamine (0.578 mL, 4 mmol) followed by o-fluorobenzoyl chloride (1 g, 4 mmol). Stir the reaction for 1 hour at room temperature. Add an additional amount of methylene chloride (25 mL) and stir overnight. Dilute the reaction with ethyl acetate (100 mL), wash with water (100 mL) and dry the organic phase. Concentrate in vacuo and recrystallize the residue from ethyl acetate/hexane to yield the title compound (1.05 g, 67%); mp >290° C.

Workup

  1. customthe reaction for 1 hour at room temperature
  2. stirringstir overnight
  3. additionDilute
  4. washwash with water (100 mL)
  5. customdry the organic phase
  6. concentrationConcentrate in vacuo
  7. customrecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-806699b3647440b39c6beb2ae2d45d8e
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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