Dimethylformamide → HCID 75153691, compound

HRID 576037Notes

Reaction equation

HRID 576037 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[F:18][C:19]([F:37])([F:36])[C:20]1[CH:21]=[C:22]([C:30](=O)[C:31]([F:34])([F:33])[F:32])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1.[OH-].[Ca+2].[OH-].CN(C)C=O>COC(C)(C)C>[F:18][C:19]([F:36])([F:37])[C:20]1[CH:21]=[C:22]([C:30]([C:31]([F:34])([F:33])[F:32])=[CH:2][C:1]([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:5]=2)=[O:3])[CH:23]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6093208Calcium HydroxideHCID 462223851-Naphthalenecarboxylic acid, 4-acetyl-, methyl esterHCID 46222386HCID 46222386, compound

Product 1

HCID 75153691HCID 75153691, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of methyl 4-acetyl-1-naphthalenecarboxylate (5.36 g, 23.5 mmol), 1-[3,5-bis(trifluoromethyl)phenyl]-2,2,2-trifluoroethanone (7.28 g, 23.5 mmol), calcium hydroxide (1.40 g, 18.9 mmol), N,N-dimethylformamide (16 mL) and tert-butyl methyl ether (32 mL) was boiled with provision of the apparatus comprising a ten-plate Oldershaw column and decanter described in Example 1, Step A for removal of the tert-butyl methyl ether/water azeotrope. As the decanter trap contained an amount of tert-butyl methyl ether sufficient to dissolve all of the water formed by the reaction, the condensate in the trap did not separate into layers containing predominately water and predominately tert-butyl methyl ether. Tert-butyl methyl ether was removed by gradually draining the decanter trap until the pot temperature was 85° C. To maintain this temperature, tert-butyl methyl ether was added as needed to compensate for loss of solvent from the apparatus. The total time from beginning heating the reaction mixture to stopping distillation, not including a shutdown period overnight, was about 10 h. During this time period no additional calcium hydroxide was added to the reaction mixture.

Workup

  1. customdescribed in Example 1, Step A for removal of the tert-butyl methyl ether/water azeotrope
  2. dissolutionto dissolve all of the water
  3. customformed by the reaction
  4. customthe condensate in the trap did not separate into layers
  5. additioncontaining predominately water and predominately tert-butyl methyl ether
  6. customTert-butyl methyl ether was removed
  7. customwas 85° C
  8. temperatureTo maintain this temperature, tert-butyl methyl ether
  9. additionwas added
  10. temperatureThe total time from beginning heating the reaction mixture
  11. distillationdistillation
  12. customa shutdown period overnight
  13. additionDuring this time period no additional calcium hydroxide was added to the reaction mixture

Sources & evidence

ORD record
ord-76a2c5629f09410ea41d4c6978ac48f3
Source dataset
uspto-grants-2015_05
Patent number
US09035101B2

Reaction notes

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