Aluminum(III) Chloride → HCID 172035639, compound

HRID 2309116Notes

Reaction equation

HRID 2309116 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]([CH:38]=[CH:39][CH:40]=3)[O:20][C:21]3[N:25](CC4C=CC(OC)=CC=4)[N:24]=[N:23][C:22]=3[C:35](O)=[O:36])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:40]=[CH:39][C:38]4[C:35](=[O:36])[C:22]5[NH:23][N:24]=[N:25][C:21]=5[O:20][C:19]=4[CH:18]=3)[CH2:11][CH2:12]2)=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 20186857HCID 20186857, compound

Product 1

HCID 172035639HCID 172035639, compoundYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

The carboxylic acid from example 3 (150 mg, 0.25 mmole), was converted to its acid chloride using the same procedure as described. The acid chloride was suspended in dry dichloromethane, (10 ml), and the mixture stirred at -20° C. Aluminium chloride, (127 mg, 0.95 mmole), was added portionwise to the mixture and stirring continued for 2 hours at -20° C. The reaction was warmed to 0° C. over 1 hour, then stirred for 2 hours at 0° C., then quenched with dilute hydrochloric acid, (20 ml). After standing overnight the mixture was decanted and the residual orange gum was washed with a little water and triturated with hot methanol. Filtration of the cooled mixture gave 20 mg (16%) of the title compound as its hydrochloride. The free base was obtained by suspending the solid in water, neutralizing to pH 7 with dilute sodium hydrogen carbonate solution and filtering off the pale orange solid. After drying in vacuo 14 mg (12%) of the title compound was isolated.

Workup

  1. stirringstirring
  2. temperatureThe reaction was warmed to 0° C. over 1 hour
  3. stirringstirred for 2 hours at 0° C.
  4. customquenched with dilute hydrochloric acid, (20 ml)
  5. waitAfter standing overnight
  6. customthe mixture was decanted
  7. washthe residual orange gum was washed with a little water
  8. customtriturated with hot methanol
  9. filtrationFiltration of the cooled mixture

Sources & evidence

ORD record
ord-561521460eba47d59403877ac69cff08
Source dataset
uspto-grants-1987_09
Patent number
US04692526

Reaction notes

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