Hexane → HCID 21460677, compound

HRID 2082520Notes

Reaction equation

HRID 2082520 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].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[CH2:28](N(CC)CC)C.CCCCCC>C(Cl)Cl.C(OCC)(=O)C>[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](=[O:24])[CH2:28][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:21][CH:20]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8471Triethylamine2×HCID 678794-Fluorobenzoyl chloride2×HCID 15043966HCID 15043966, compound

Product 1

HCID 21460677HCID 21460677, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (2.0 g, 7.13 mmol) in methylene chloride (125 mL) and add p-fluorobenzoyl chloride (0.886 mL, 7.5 mmol) followed by triethylamine (1.05 mL, 7.5 mmol). Stir the reaction at room temperature overnight. Add an additional amount of p-fluorobenzoyl chloride (0.20 mL) and triethylamine (0.20 mL) and stir for 6 hours. Dilute the reaction with ethyl acetate, wash with 1N HCl, saturated sodium bicarbonate, saturated sodium chloride, dry over magnesium sulfate, filter and concentrate, in vacuo give a solid. Dissolve the solid in hot ethyl acetate (250 mL), reduce to 200 mL and add hot hexane (50 mL). Cool the solution and collect to resulting solid to yield the title compound as fluffy white crystals (1.52 g, 53%); 241°-243° C.

Workup

  1. customthe reaction at room temperature overnight
  2. stirringstir for 6 hours
  3. additionDilute
  4. washwash with 1N HCl, saturated sodium bicarbonate, saturated sodium chloride
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate, in vacuo
  8. customgive a solid
  9. temperatureCool the solution
  10. customcollect
  11. customto resulting solid

Sources & evidence

ORD record
ord-d0d5d7bedcdd453596a189225d233d8b
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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