Potassium Carbonate → HCID 21452885, compound

HRID 436642Notes

Reaction equation

HRID 436642 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1.[CH3:15][CH:16]([NH2:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([NH2:24])[CH3:23].[C:26](=[O:29])([O-])[O-].[K+].[K+]>C(Cl)CCl>[CH3:23][CH:22]([NH:24][C:26](=[O:29])[C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:13])[F:14])=[CH:12][CH:11]=1)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([NH:25][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=1)[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 19967927HCID 19967927, compound

Product 1

HCID 21452885HCID 21452885, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution containing 12.8 g. of 4-trifluoromethoxybenzoyl chloride in 50 ml. of ethylene dichloride was added dropwise with stirring to a mixture of 4.50 g. of 2,8-nonanediamine, 8.42 g. of potassium carbonate and 100 ml. of ethylene dichloride, the latter mixture being at 10° C. The reaction mixture was stirred while allowing its temperature to rise to room temperature (about 25°-30° C.) and was then stored at 5° C. overnight (about sixteen hours). The precipitated white solid was collected, washed well with water and dried to yield 12.2 g. of white needles. The filtrate was separated and the aqueous portion was extracted with one 100 ml. portion of ethylene dichloride. The extract was combined with the ethylene dichloride portion of the filtrate and the combined solution was dried successively over anhydrous sodium sulfate and anhydrous potassium carbonate. Removal of the solvent under reduced pressure left 2.6 g. of a pale yellow oil which completely crystallized on standing at room temperature. The 12.2 and 2.6 g. portions of crystalline product were combined and recrystallized from 95% ethanolbenzene and dried in vacuo at 50° C. for eighteen hours to yield 11.5 g of N,N'-(1,7-dimethylheptamethylene)bis(4-trifluoromethoxybenzamide), m.p. 156°-160° C.

Workup

  1. additionA solution containing 12.8 g
  2. custombeing at 10° C
  3. stirringThe reaction mixture was stirred
  4. customto rise to room temperature
  5. custom(about 25°-30° C.)
  6. custom(about sixteen hours)
  7. customThe precipitated white solid was collected
  8. washwashed well with water
  9. customdried
  10. customto yield 12.2 g
  11. customThe filtrate was separated
  12. extractionthe aqueous portion was extracted with one 100 ml
  13. dry with materialthe combined solution was dried successively over anhydrous sodium sulfate and anhydrous potassium carbonate
  14. customRemoval of the solvent under reduced pressure
  15. waitleft 2.6 g
  16. customof a pale yellow oil which completely crystallized
  17. customon standing at room temperature
  18. customrecrystallized from 95% ethanolbenzene
  19. customdried in vacuo at 50° C. for eighteen hours

Sources & evidence

ORD record
ord-08b6e838da784a8da25848f8c41d0003
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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