Benzoyl chloride → HCID 21460685, compound

HRID 2082503Notes

Reaction equation

HRID 2082503 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH2:19](N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCC)(=O)C>O1CCCC1>[CH2:19]([NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:33]

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21460705HCID 21460705, compound

Product 1

HCID 21460685HCID 21460685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Suspend the 3-amino-2-carbethoxy-6-nitroindole (0.6 mmol) in tetrahydrofuran (mL) and add triethylamine (0.62 mmol). Add benzoyl chloride (0.62 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-nitroindole.

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-3d8153e6ddb346748b58556ccbc2621e
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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