1,2-Dichloroethane → 9-ethyl-9H-carbazole-3,6-dicarbaldehyde

HRID 1954657Notes

Reaction equation

HRID 1954657 reaction equation
CN([CH:4]=[O:5])C.P(Cl)(Cl)(Cl)=[O:7].[CH2:11]([N:13]1[C:25]2[CH:24]=[CH:23]C=[CH:21][C:20]=2[C:19]2[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12].Cl[CH2:27][CH2:28]Cl>>[CH2:11]([N:13]1[C:14]2[CH:15]=[CH:16][C:17]([CH:4]=[O:5])=[CH:18][C:19]=2[C:20]2[C:25]1=[CH:24][CH:23]=[C:27]([CH:28]=[O:7])[CH:21]=2)[CH3:12]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 6836N-ethyl carbazoleHCID 24813Phosphorus oxychloride

Product 1

HCID 37166759-ethyl-9H-carbazole-3,6-dicarbaldehydeYield 40%

Procedure

109 g of DMF was cooled down to 0° C., and 228 g of phosphorous oxychloride was slowly dropped therein. The resultant was heated up to room temperature, and then 30 g of N-ethylcarbazole and 75 ml of 1,2-dichloroethane were dropped therein. The reaction of the mixture was carried out at 90° C. for 20 hours, thereafter the solution was cooled down to room temperature. The solution was poured into 1.5 l of ice water, and extracted with chloroform, dried with anhydrous MgSO4, and was separated with hexane and ethyl acetate in a column. The reaction yield was about 40%. The structure analysis was confirmed by 1H-NMR, which was shown in FIG. 6.

Workup

  1. customThe reaction of the mixture
  2. temperaturethe solution was cooled down to room temperature
  3. extractionextracted with chloroform
  4. dry with materialdried with anhydrous MgSO4
  5. customwas separated with hexane and ethyl acetate in a column
  6. customThe reaction yield was about 40%

Sources & evidence

ORD record
ord-3986f67dc9174634841918f7a8a49b19
Source dataset
uspto-grants-2000_09
Patent number
US06124046

Reaction notes

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