Carbon Tetrachloride → ethyl 5-bromo-8-carbamoyl-6-chloro-9H-carbazole-2-carboxylate

HRID 523203Notes

Reaction equation

HRID 523203 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][C:9]=1[NH:10]2.C(Cl)(Cl)(Cl)[Cl:24].C1C(=O)N(Cl)C(=O)C1>CN1C(=O)CCC1>[Br:1][C:2]1[C:14]([Cl:24])=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][C:9]=1[NH:10]2

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398ChlorosuccinimideHCID 59375100ethyl 5-bromo-8-carbamoyl-9H-carbazole-2-carboxylate

Product 1

HCID 117760738ethyl 5-bromo-8-carbamoyl-6-chloro-9H-carbazole-2-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of ethyl 5-bromo-8-carbamoyl-9H-carbazole-2-carboxylate (90 g, 249 mmol), CCl4 (2900 mL), and NMP (600 mL) was added NCS (36.1 g, 271 mmol). The reaction mixture was stirred at 45° C. for 2 h. After cooling to room temperature, the solid was collected by vacuum filtration. The solid was stirred in methanol (1 L) at 60° C. for 2 h and then cooled to room temperature. The solid was collected and dried to give ethyl 5-bromo-8-carbamoyl-6-chloro-9H-carbazole-2-carboxylate (69.5 g, 167 mmol, 67% yield) (95% purity).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was collected by vacuum filtration
  3. stirringThe solid was stirred in methanol (1 L) at 60° C. for 2 h
  4. temperaturecooled to room temperature
  5. customThe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-62a63be192cc4600b32d8e9dfefdec4c
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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