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Benzoyl chloride → HCID 21460706, compound

HRID 1488819
Notes
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Reaction equation

HRID 1488819 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 15043966HCID 15043966, compound

Product 1

HCID 21460706HCID 21460706, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857
Ethyl Acetate
Solvent

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-72e7a7f9f56844eb8f8e0bd48aec2c0a
Source dataset
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05675018

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes