N-ethyl carbazole → HCID 68603125, compound

HRID 1402648Notes

Reaction equation

HRID 1402648 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[F:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:30]1([CH3:39])[C:31]([C:36](Cl)=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1>C(Cl)Cl>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:21]([C:20]3[CH:24]=[CH:25][C:17]([F:16])=[CH:18][CH:19]=3)=[O:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:36](=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH3:39])[CH:8]=2)[CH3:2]

Participants

6

Reactant 4

HCID 6836N-ethyl carbazoleHCID 678794-Fluorobenzoyl chlorideHCID 702762-Methylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 68603125HCID 68603125, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-ethylcarbazol (8.0 g) in CH2Cl2 (200 mL) is added 4-fluorobenzoyl chloride (6.5 g) and AlCl3 (5.6 g) at 0° C. After stirring overnight at room temperature, 2-toluoyl chloride (6.5 g) and AlCl3 (6.0 g) are further added at 0° C. and the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with H2O and brine, dried over MgSO4, and concentrated to give the residue, which is used for the next step without further purification. The structure of the product, which is obtained as a beige solid, is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.52 (t, 3H), 2.35 (s, 3H), 4.46 (q, 2H), 7.20 (t, 2H), 7.27-7.46 (m, 4H), 7.50 (t, 2H), 7.86 (d, 1H), 7.88 (d, 1H), 8.02 (d, 1H), 8.07 (d, 1H), 8.54 (s, 1H), 8.55 (s, 1H).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionthe crude product is extracted twice with CH2Cl2
  3. washThe combined organic layer is washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customis used for the next step without further purification
  8. customThe structure of the product, which is obtained as a beige solid

Sources & evidence

ORD record
ord-91a23f3324e54a63898e35b1abf4c83c
Source dataset
uspto-grants-2014_12
Patent number
US08911921B2

Reaction notes

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