Hexane → HCID 21460677, compound

HRID 2396358Notes

Reaction equation

HRID 2396358 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(OC(=O)C)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 reactionat 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 sodiumbicarbonate, saturated sodium chloride, dry over magnesium sulfate, filter and concentrate, in vacuo to give a solid. Dissolve the solid in hot ethylacetate (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. stirringstir for 6 hours
  2. additionDilute
  3. washwash with 1N HCl, saturated sodiumbicarbonate, saturated sodium chloride
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate, in vacuo
  7. customto give a solid
  8. temperatureCool the solution
  9. customcollect
  10. customto resulting solid

Sources & evidence

ORD record
ord-cfb57ef891854b308b80892c1d0248b8
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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