N-ethyl carbazole → 3,6-Bis(4-chlorobutyryl)-N-ethylcarbazole

HRID 1658107Notes

Reaction equation

HRID 1658107 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].[Cl:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21].[Cl-:23].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]([C:7]1[CH:6]=[CH:5][C:4]2[N:3]([CH2:1][CH3:2])[C:15]3[C:10]([C:9]=2[CH:8]=1)=[CH:11][C:12]([C:20](=[O:21])[CH2:19][CH2:18][CH2:17][Cl:23])=[CH:13][CH:14]=3)=[O:21]

Participants

5

Reactant 3

HCID 6836N-ethyl carbazoleHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 123317903,6-Bis(4-chlorobutyryl)-N-ethylcarbazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 78.0 g (0.4 mole) of 9-ethylcarbazole and 141 g (1.0 mole) of 4-chlorobutyryl chloride in 1 liter of methylene chloride, which has been previously chilled to 0°C, is added portionwise 127.0 g (0.95 mole) of aluminum chloride. The mixture is stirred at room temperature for 16 hours, and the resulting complex is decomposed with a concentrated hydrochloric acid-ice mixture. The organic layer is separated, washed with water, dried over magnesium sulfate and pentane added to precipitate the desired product. Recrystallization from acetone followed by a recrystallization from an acetone methanol solution results in the formation of 3,6-bis (4-chlorobutyryl)-9-ethylcarbazole, m.p. 106°-8°C; λmaxEtOH 259; and E1cm1% 1030.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate and pentane
  4. additionadded
  5. customto precipitate the desired product
  6. customRecrystallization from acetone
  7. customfollowed by a recrystallization from an acetone methanol solution

Sources & evidence

ORD record
ord-63043210efe843f18eef2032be8f290b
Source dataset
uspto-grants-1976_06
Patent number
US03962451

Reaction notes

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