4-Chlorobenzoyl chloride → HCID 53799429, compound

HRID 843900Notes

Reaction equation

HRID 843900 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([N:15]([CH3:17])[CH3:16])[CH2:6][C:5]2=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10]2[CH2:9][CH2:8][CH:7]([N:15]([CH3:17])[CH3:16])[CH2:6][C:5]3=2)=[O:24])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 226115606-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole

Product 1

HCID 53799429HCID 53799429, compoundYield 17.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 10.6 mg (0.046 mMol) 6-amino-3-(dimethyl)amino-1,2,3,4-tetrahydro-9H-carbazole and 14.0 mg (0.12 mMol) polyvinylpyridine in 3.0 mL dichloromethane were added 8.8 μL (0.069 mMol) 4-chlorobenzoyl chloride. The reaction mixture was mixed for 1 day at ambient temperature. To this mixture were then added 160 mg (0.128 mMol) aminomethylated polystyrene and the reaction mixed for an additional 18 hours. The reaction mixture was diluted with 1.0 mL methanol, treated with potassium carbonate, and filtered through a short column of sodium sulfate. The filtrate was then evaporated to give 2.9 mg (17%) of the title compound as a beige solid.

Workup

  1. additionThe reaction mixture was mixed for 1 day at ambient temperature
  2. additionTo this mixture were then added 160 mg (0.128 mMol)
  3. additionthe reaction mixed for an additional 18 hours
  4. filtrationfiltered through a short column of sodium sulfate
  5. customThe filtrate was then evaporated

Sources & evidence

ORD record
ord-839cc193315449ae97e8d122bfbccd7b
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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