Benzoyl chloride → HCID 21460729, compound

HRID 2396338Notes

Reaction equation

HRID 2396338 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH2:20](N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OCC)(=O)C>O1CCCC1>[CH2:20]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([F:14])([F:12])[F:13])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:34]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21460740HCID 21460740, compound

Product 1

HCID 21460729HCID 21460729, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Suspend the 3-amino-2-carbethoxy-6-trifluoromethylindole (290 mg, 1.06 mmol) in tetrahydrofuran (30 mL) and add triethylamine (0.150 mL, 1.17 mmol). Add benzoyl chloride (0.136 mL, 1.17 mmol) and stir for 30 minutes at room temperature. Dilute the reaction with ethyl acetate (mL), rinse with 1M HCl, water, dry over magnesium sulfate, filter and concentrate in vacuo. Recrystallize from hot ethyl acetate/hexane to yield 3-[(phenacyl)amino]-2-carbethoxy-6-trifluoromethylindole (230 mg, 56%); mp237°-239° C.

Workup

  1. additionDilute
  2. washrinse with 1M HCl, water
  3. dry with materialdry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customRecrystallize from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-f9ddd2c83cfe48c39282d4d43659bd83
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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