Water → HCID 52916772, compound

HRID 1028320Notes

Reaction equation

HRID 1028320 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]3[CH2:19][O:18]3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[N-:20]=[N+:21]=[N-:22].[Na+].[NH4+].[Cl-].O>CCO>[N:20]([CH2:19][CH:17]([OH:18])[CH2:16][N:6]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)=[N+:21]=[N-:22]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

Product 1

HCID 52916772HCID 52916772, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole (500 mg, 1.3 mmol), NaN3 (111 mg, 1.7 mmol), NH4Cl (91 mg, 1.7 mmol), were combined in 4 ml of EtOH and 1 ml of H2O and heated to 80° C. overnight. Upon completion, the EtOH was evaporated and the mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine and dried over Na2SO4 and concentrated. The material was used in the next step without further purification.

Workup

  1. customUpon completion, the EtOH was evaporated
  2. customthe mixture was partitioned between EtOAc and H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe material was used in the next step without further purification

Sources & evidence

ORD record
ord-2bc8aa8c7b954b0fa3b728e4c66da3c4
Source dataset
uspto-grants-2014_05
Patent number
US08735440B2

Reaction notes

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