Triethylamine → HCID 21460730, compound

HRID 2396370Notes

Reaction equation

HRID 2396370 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.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1.C(OCC)(=O)C>C(Cl)Cl>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](=[O:31])[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:28][CH:27]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 8857Ethyl AcetateHCID 15043966HCID 15043966, compound

Product 1

HCID 21460730HCID 21460730, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (2.2 g, 8 mmol) in methylene chloride (70 mL) and add triethylamine (1.16 mL, 8 mmol) followed by p-chlorobenzoyl chloride (0.976 mL, 8 mmol). Stir the reaction48 hours at room temperature. Dilute the reaction with ethyl acetate (300 mL), wash with water (100 mL), dry the organic phase over magnesium sulfate, filter and concentrate in vacuo. Recrystallize the residue from ethyl acetate/hexane to yield the title compound as a fluffy solid (2.7 g,79%).

Workup

  1. additionDilute
  2. washwash with water (100 mL)
  3. dry with materialdry the organic phase over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customRecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-320851294e99432e8225154bffaa1f03
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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