Water → HCID 57257503, compound

HRID 1420703Notes

Reaction equation

HRID 1420703 reaction equation
[CH:1]1[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.[H-].[Na+].[OH2:16].CN([CH:20]=[O:21])C>>[CH:10]1[C:11]2[N:12]([CH2:4][C@H:5]([CH3:6])[CH2:13][O:16][CH:10]3[CH2:9][CH2:8][CH2:7][CH2:20][O:21]3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6854CarbazoleHCID 24758Sodium hydride

Product 1

HCID 57257503HCID 57257503, compoundYield 21%

Procedure

Carbazole (1.42 g, 0.0085 mol) was dissolved in dry DMF (40 mL) and NaH (60% dispersion in oil) (0.443 g, 0.0111 mol) was added. After stirring at ambient temperature for 45 min compound 8 (2.02 g, 0.0085 mol) was added and stirring continued at room temperature for 18 h. Water (20 mL) was added. Extraction with CH2Cl2 (3×20 ml), drying of the organic phases (MgSO4) and evaporation of the solvents in vacuo afforded an oil. Purification of the crude product twice on a silica gel column (1: Eluent: ethyl acetate/n-heptane(1:8), and 2: Eluent: ethyl acetate/toluene (1:9)) gave the title compound 0.59 g (21%) as an oil.

Workup

  1. additionwas added
  2. extractionExtraction with CH2Cl2 (3×20 ml)
  3. dry with materialdrying of the organic phases (MgSO4) and evaporation of the solvents in vacuo
  4. customafforded an oil
  5. customPurification of the crude product twice on a silica gel column (1: Eluent: ethyl acetate/n-heptane(1:8), and 2: Eluent: ethyl acetate/toluene (1:9))

Sources & evidence

ORD record
ord-ba55337eb1634383b6c0c2616f9f9d42
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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