Hydrochloric Acid → HCID 633805, compound

HRID 1578088Notes

Reaction equation

HRID 1578088 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH:11]1[CH2:16][C:15](=O)[CH2:14][C:13](=[O:18])[CH2:12]1.[Cl:19][C:20]1[CH:31]=[C:24]2[C:25](OC(=O)[NH:29][C:23]2=[CH:22][CH:21]=1)=[O:26].Cl>CN(C)C=O>[Cl:19][C:20]1[CH:31]=[C:24]2[C:23]([NH:29][C:15]3[CH2:16][CH:11]([C:5]4[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=4[Cl:3])[CH2:12][C:13](=[O:18])[C:14]=3[C:25]2=[O:26])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 784805-Chloroisatoic anhydrideHCID 5991285-(2,4-dichlorophenyl)cyclohexane-1,3-dione

Product 1

HCID 633805HCID 633805, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of 0.96 g of 50% sodium hydride in 10 ml of N,N-dimethylformamide at -10° C. is added dropwise a solution of 5.14 g of 5-(2,4-dichlorophenyl)cyclohexan-1,3-dione in 40 ml of N,N-dimethylformamide. During the addition frothing occurs and the temperature rises to 10° C. The mixture is then stirred at room temperature for 1 hr and cooled to 5° C. A solution of 3.96 g of 5-chloroisatoic anhydride in 40 ml of N,N-dimethylformamide is added and stirring is continued at room temperature for 18 hrs and then at 85°-90° C. for 5 hr. The mixture is poured into 1300 ml of ice water containing 10 ml of concentrated hydrochloric acid. The solid is collected, washed with water, and suspended in 200 ml of methanol. The suspension is heated on a steam bath for 0.5 hr, cooled and filtered. The solid is washed with methanol and then with ether and dried in vacuo at 60° C. for 18 hrs to give 7-chloro-3-(2,4-dichlorophenyl)-3,4-dihydro-1,9(2H,10H)-acridinedione; mp 308°-310° C.

Workup

  1. customrises to 10° C
  2. temperaturecooled to 5° C
  3. stirringstirring
  4. waitis continued at room temperature for 18 hrs
  5. waitat 85°-90° C. for 5 hr
  6. customThe solid is collected
  7. washwashed with water
  8. temperatureThe suspension is heated on a steam bath for 0.5 hr
  9. temperaturecooled
  10. filtrationfiltered
  11. washThe solid is washed with methanol
  12. dry with materialwith ether and dried in vacuo at 60° C. for 18 hrs

Sources & evidence

ORD record
ord-b5fe624ae1f14ee99b6d99d91995c2c6
Source dataset
uspto-grants-1981_09
Patent number
US04291034

Reaction notes

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