Water → HCID 68156295, compound

HRID 1485580Notes

Reaction equation

HRID 1485580 reaction equation
[C:1]1([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:31])C(=O)C1.O>CN(C=O)C>[Br:31][C:3]1[CH:2]=[C:1]([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])[C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 68156244HCID 68156244, compound

Product 1

HCID 68156295HCID 68156295, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

62 g (207 mmol) of methyl 2-(9H-carbazolyl)benzoate are cooled to −10° C. in 2 l of DMF, and 37.3 g (207 mmol) of NBS are added in portions. The solution is then brought to room temperature and stirred at this temperature for 6 h. 500 ml of water are subsequently added to the mixture, which is then extracted with CH2Cl2. The organic phase is dried over MgSO4, and the solvents are removed in vacuo. The product is washed by stirring with hot toluene, and the solid is isolated.

Workup

  1. customis then brought to room temperature
  2. extractionis then extracted with CH2Cl2
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvents are removed in vacuo
  5. washThe product is washed
  6. stirringby stirring with hot toluene
  7. customthe solid is isolated

Sources & evidence

ORD record
ord-2791152b25784aa08cf151d95db68e44
Source dataset
uspto-grants-2016_08
Patent number
US09422287B2

Reaction notes

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