Benzoyl chloride → HCID 21460729, compound

HRID 2082500Notes

Reaction equation

HRID 2082500 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 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%); mp 237°-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-5793611315fb44779a5fc445e790a54a
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

Loading…