Benzoyl chloride → HCID 21460706, compound

HRID 2082506Notes

Reaction equation

HRID 2082506 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].[CH2:18](N(CC)CC)C.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl.C(OCC)(=O)C>[CH2:18]([NH: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])[C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:32]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 15043966HCID 15043966, compound

Product 1

HCID 21460706HCID 21460706, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-amino-2-carbethoxy-4,6-dichloroindole (7.8 g, 27.8 mmol) in methylene chloride (500 mL) and add triethylamine (4.2 mL, 30 mmol) followed by benzoyl chloride (3.5 mL, 30 mmol). Stir at room temperature overnight. Dilute with ethyl acetate (300 mL), wash with water and separate the organic phase. Dry (MgSO4) and evaporate the solvent in vacuo to give a solid. Recrystallize (ethyl acetate) to give the title compound as off-white needles (7.75 g, 74%).

Workup

  1. washwash with water
  2. customseparate the organic phase
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. customto give a solid
  6. customRecrystallize (ethyl acetate)

Sources & evidence

ORD record
ord-7aed7cea0e09477ea141691efe3dc4db
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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