Benzoyl chloride → HCID 21460679, compound

HRID 2082544Notes

Reaction equation

HRID 2082544 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18](N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)(=O)C>C(Cl)Cl>[CH2:18]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:12])=[C:8]([Cl:11])[CH:9]=2)[NH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:32]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21460704HCID 21460704, compound

Product 1

HCID 21460679HCID 21460679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-amino-2-carbethoxy-5,6-dichloroindole (2.2 g, 8 mmol) in methylene chloride (70 mL) and add triethylamine (1.16 mL, 8 mmol) followed by benzoyl chloride (0.93 mL, 8 mmol). Stir the reaction 48 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.

Workup

  1. customthe reaction 48 hours at room temperature
  2. additionDilute
  3. washwash with water (100 mL)
  4. dry with materialdry the organic phase over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customRecrystallize the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-13fdba1306434ef4a9bb5715ef9d8072
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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