Water → HCID 69283695, compound

HRID 1293450Notes

Reaction equation

HRID 1293450 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.O.CN([CH:20]=[O:21])C>O=P(Cl)(Cl)Cl>[CH:20]([N:14]1[C:15]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[C:8]2[C:13]1=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 6228Dimethylformamide2×HCID 107743051-methoxy-9H-carbazole

Product 1

HCID 69283695HCID 69283695, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
0 °C

Procedure

In a 50 mL round bottomed flask was dissolved POCl3 (0.6 mL, 15.23 mM) in 20 mL of dry DMF. The reaction mixture was stirred at 0° C. in an ice bath. To this was added slowly, 1-methoxy-9H-carbazole (1 g, 5.07 mM) dissolved in 30 mL of dry DMF. The reaction mixture was stirred for 2 hrs. Water was added to the reaction mixture and the precipitated product was filtered off. The residue was dissolved in EtOAc and was washed with brine and dried over anh. Na2SO4. Ethyl acetate was then evaporated to obtain the desired product as a white fluffy solid with a yield of 96% (1.1 g); mp 161-163° C.

Workup

  1. additionTo this was added slowly
  2. stirringThe reaction mixture was stirred for 2 hrs
  3. filtrationthe precipitated product was filtered off
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwas washed with brine
  6. dry with materialdried over anh. Na2SO4
  7. customEthyl acetate was then evaporated

Sources & evidence

ORD record
ord-7557f0b913a1412abfd3ce55d2f414b8
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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