Hydrochloric Acid → HCID 45381113, compound

HRID 1615041Notes

Reaction equation

HRID 1615041 reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH3:2].[Al+3].[Cl-:22].[Cl-].[Cl-].[Cl:25][CH2:26][CH2:27][C:28](Cl)=[O:29].Cl>ClCCl>[ClH:25].[Cl:25][CH2:26][CH2:27][C:28]([C:15]1[CH:16]=[CH:17][C:18]2[N:6]([CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:19][CH3:20])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([C:28](=[O:29])[CH2:27][CH2:26][Cl:22])=[CH:9][CH:8]=3)=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 58544901HCID 58544901, compound

Product 1

HCID 45381113HCID 45381113, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-(2-Diethylaminoethyl)carbazole (68) (17.9 g, 67.3 mmol, 1 eq) was dissolved in dry dichloromethane (150 mL). Anhydrous AlCl3 (45 g, 337 mmol, 5 eq) was added portion-wise with stirring and cooling in an ice bath. 3-chloro-propionyl chloride (32.4 mL, 337 mmol, 5 eq) was added dropwise, while maintaining the internal temperature below 5° C. The reaction mixture was stirred at this temperature for 15 h, poured into cold 3% HCl (violent foaming should be avoided) and extracted with CHCl3 (5×500 mL). The extracts were evaporated and the resulted green oil triturated with diethyl ether (5×50 mL) to give 24 g (74%) of 3,6-di(3-chloropropionyl)-9-(2-diethylaminoethyl)-carbazole hydrochloride (69) as dark grey solid.

Workup

  1. temperaturecooling in an ice bath
  2. temperaturewhile maintaining the internal temperature below 5° C
  3. stirringThe reaction mixture was stirred at this temperature for 15 h
  4. extractionextracted with CHCl3 (5×500 mL)
  5. customThe extracts were evaporated
  6. customthe resulted green oil triturated with diethyl ether (5×50 mL)

Sources & evidence

ORD record
ord-07a37388a2e84f589348d8b4c6fc52eb
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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