Diisopropyl Ether → HCID 20335994, compound

HRID 1706403Notes

Reaction equation

HRID 1706403 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.C(N(CC)CC)C.[Cl:21]C(OCC)=O.[CH2:27]([N:29]1[CH2:33][CH:32]([NH2:34])[CH2:31][N:30]1[CH2:35][CH3:36])[CH3:28].C(OC(C)C)(C)C>C(Cl)Cl>[ClH:11].[ClH:21].[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:34][CH:32]2[CH2:31][N:30]([CH2:35][CH3:36])[N:29]([CH2:27][CH3:28])[CH2:33]2)=[O:8])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

7

Reactant 5

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 5591991,2-Diethyl-4-pyrazolidinamine

Product 1

HCID 20335994HCID 20335994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-sodium chloride chilled stirring suspension of 46.34 g. (0.23 mole) of 4-amino-5-chloro-2-methoxybenzoic acid in 400 ml. of methylene chloride was added 23.23 g. (0.23 mole) of triethylamine. After the temperature had fallen to 0° C., 24.96 g. (0.23 mole) of ethyl chloroformate was added dropwise while maintaining a temperature of 0°-5° C. by ice bath cooling. The mixture was stirred at this temperature for 1 hour. To this was added dropwise at 0°-5° C. a solution of 32.26 g. (0.23 mole) of 1,2-diethyl-4-pyrazolidinamine in methylene chloride and stirring was continued for 0.5 hour at this temperature. The resulting mixture was washed with a dilute solution of sodium bicarbonate and the methylene chloride dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in 2-propanol, filtered, and made acidic to litmus by bubbling hydrogen chloride gas through the solution. The product was recrystallized from a mixture of ethanol, 2-propanol and isopropyl ether. A yield of 34.6 g. of product which melted at 182°-185° C. was obtained. To the filtrate was added additional isopropyl ether and after chilling, 15.35 g. of product which melted at 179°-185° C. was obtained. The combined yield was 49.95 g. (50%).

Workup

  1. additionsuspension of 46.34 g
  2. customhad fallen to 0° C.
  3. temperaturewhile maintaining a temperature of 0°-5° C. by ice bath
  4. temperaturecooling
  5. stirringThe mixture was stirred at this temperature for 1 hour
  6. additionTo this was added dropwise at 0°-5° C. a solution of 32.26 g
  7. washThe resulting mixture was washed with a dilute solution of sodium bicarbonate
  8. dry with materialthe methylene chloride dried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue was dissolved in 2-propanol
  12. filtrationfiltered
  13. customby bubbling hydrogen chloride gas through the solution
  14. customThe product was recrystallized from a mixture of ethanol, 2-propanol and isopropyl ether
  15. customof product which melted at 182°-185° C. was obtained
  16. temperatureafter chilling
  17. customof product which melted at 179°-185° C. was obtained

Sources & evidence

ORD record
ord-c9f3346bb2be4c6d8c1d6d0c890c236c
Source dataset
uspto-grants-1980_06
Patent number
US04207327

Reaction notes

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