Benzoyl chloride → HCID 21460729, compound

HRID 1941412Notes

Reaction equation

HRID 1941412 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%); 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-f39253319ca4462fa3e055dabaf7cd2c
Source dataset
uspto-grants-1997_12
Patent number
US05703107

Reaction notes

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