Triethylamine → HCID 21460712, compound

HRID 2396368Notes

Reaction equation

HRID 2396368 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]([F:37])([F:36])[C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.C(OCC)(=O)C>C(Cl)Cl>[F:25][C:26]([F:37])([F:36])[C:27]1[CH:35]=[CH:34][C:30]([C:31](=[O:32])[CH2:18][NH:1][C:2]2[C:10]3[C:5](=[CH:6][C:7]([Cl:12])=[CH:8][C:9]=3[Cl:11])[NH:4][C:3]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 15043966HCID 15043966, compound

Product 1

HCID 21460712HCID 21460712, compound

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 p-trifluoromethylbenzoyl chloride (0.488 mL, 4 mmol). Stir thereaction 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 as a white fluffy solid (1.42 g, 80%); mp 250°-252° C.

Workup

  1. stirringstir overnight
  2. additionDilute
  3. washwash with water (100 mL)
  4. customdry the organic phase
  5. concentrationConcentrate in vacuo
  6. customrecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0a47322be36c42eba27aa161f22b75e2
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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