Methanesulfonic Acid → HCID 86637942, compound

HRID 1879321Notes

Reaction equation

HRID 1879321 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=O)[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)(Cl)=O.[OH-].[Na+].[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[O:9][CH3:10])[C:14]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)([CH2:35][S:36]([OH:39])(=[O:38])=[O:37])[NH:13][CH2:12][CH2:11]2

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 27282117N-[2-(3,4-dimethoxyphenyl)ethyl]-3-[4-(trifluoromethyl)phenyl]propanamide

Product 1

HCID 86637942HCID 86637942, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

The compound 3 is suspended in toluene and heated to 80-100° C. After addition of 1.5 equivalents phosphorus oxychloride the mixture is heated for 6 hours to 80-100° C. and then cooled within 3 hours to 20° C. The suspension is added to water while maintaining the pH of the aqueous layer during addition and subsequent stirring between 7-8 by addition of a sodium hydroxide solution. The mixture is stirred until all precipitate is dissolved. After phase separation the water is removed by azeotropic distillation. Then 1.0 equivalent of methanesulfonic acid is added, the formed suspension stirred for some time and then slowly cooled to 0-10° C. and stirred at this temperature for another couple of hours. After filtration the product is washed with toluene and dried in vacuo.

Workup

  1. temperatureis heated for 6 hours to 80-100° C.
  2. temperaturecooled within 3 hours to 20° C
  3. temperaturewhile maintaining the pH of the aqueous layer
  4. additionduring addition
  5. dissolutionis dissolved
  6. customAfter phase separation the water
  7. customis removed by azeotropic distillation
  8. stirringthe formed suspension stirred for some time
  9. temperatureslowly cooled to 0-10° C.
  10. stirringstirred at this temperature for another couple of hours
  11. filtrationAfter filtration the product
  12. washis washed with toluene
  13. customdried in vacuo

Sources & evidence

ORD record
ord-5772ada4605343a7bc744b89b0d44d59
Source dataset
uspto-grants-2012_11
Patent number
US08314238B2

Reaction notes

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