Hydrochloric Acid → N-{2-[3,6-bis(3-chloropropanoyl)-9H-carbazol-9-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 514775Notes

Reaction equation

HRID 514775 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-:28])=[O:27])(=[O:19])=[O:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-:30].[Cl-].[Cl-].[Cl:33][CH2:34][CH2:35][C:36](Cl)=[O:37].Cl>C1([N+]([O-])=O)C=CC=CC=1>[Cl:33][CH2:34][CH2:35][C:36]([C:3]1[CH:2]=[CH:1][C:13]2[N:12]([CH2:14][CH2:15][NH:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-:28])=[O:27])(=[O:18])=[O:19])[C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][C:8]([C:36](=[O:37])[CH2:35][CH2:34][Cl:30])=[CH:9][CH:10]=3)=[O:37]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 67378569HCID 67378569, compound

Product 1

HCID 86660157N-{2-[3,6-bis(3-chloropropanoyl)-9H-carbazol-9-yl]ethyl}-2-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Compound 51 (20.0 g, 50.6 mmol) was dissolved in PhNO2 (130 mL) and the solution was cooled in an ice bath. Then AlCl3 (34.0 g, 254.7 mmol) and after that, 3-chloropropionyl chloride (25.0 mL, 259.8 mmol) were added. The mixture was kept for 40 min (LC/MS monitoring), poured in a mixture of diluted HCl and ice, extracted with CHCl3, and left for 16 h. The straw-colored precipitated obtained was filtered and washed with ether. Yield of 57: 18.47 g (63%).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. extractionextracted with CHCl3
  3. waitleft for 16 h
  4. customThe straw-colored precipitated
  5. customobtained
  6. filtrationwas filtered
  7. washwashed with ether

Sources & evidence

ORD record
ord-e9d323d2412841259191177b3ef9966e
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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