Hydrochloric Acid → HCID 11965696, compound

HRID 1894039Notes

Reaction equation

HRID 1894039 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][CH2:12][O:13][CH3:14])[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH2:19].[S-2].[Na+].[Na+].Cl.C[OH:26]>>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([C:10](=[O:26])[CH2:11][CH2:12][O:13][CH3:14])[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH2:19]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14804Sodium SulfideHCID 59164526HCID 59164526, compound

Product 1

HCID 11965696HCID 11965696, compoundYield 13%

Conditions

Temperature
75 °C

Procedure

To a solution of 2-amino-5-(3-methoxy-prop-1-ynyl)-4-trifluoromethyl-benzoic acid methyl ester (1.19 g, 4.15 mmol) in MeOH (100 mL) were added successively a solution of sodium sulfide (0.1 M, 12.4 mL, 1.24 mmol), followed by 10% aq HCl-solution (3.70 mL, 12.45 mmol). The reaction mixture was heated to 75° C. for 29 h, cooled and filtered over Celite. Evaporation of the filtrate gave a yellow oil which was purified by MPLC (oRP-C18 column (particle size 5-21 μM) with 1:1 CH3CN/water. The fractions containing the product were combined, the acetonitrile was distilled off and the residual water phase was extracted with EtOAc. The organic phase was washed with brine and dried (Na2SO4) and the solvent was removed in vacuo to provide the title compound (0.167 g, 13%) as a white powder, mp 89-91° C. IR (FTIR microscope in transmission): 1696 m, 1674 s cm−1.

Workup

  1. temperaturecooled
  2. filtrationfiltered over Celite
  3. customEvaporation of the filtrate
  4. customgave a yellow oil which
  5. customwas purified by MPLC (oRP-C18 column (particle size 5-21 μM) with 1:1 CH3CN/water
  6. additionThe fractions containing the product
  7. distillationthe acetonitrile was distilled off
  8. extractionthe residual water phase was extracted with EtOAc
  9. washThe organic phase was washed with brine
  10. dry with materialdried (Na2SO4)
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e25e231be35846f38387310d65ee4e56
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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