Hydrochloric Acid → HCID 178517754, compound

HRID 2267456Notes

Reaction equation

HRID 2267456 reaction equation
[S:1]1[C:5]([C:6]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][N:9]=[C:8](SC)[N:7]=2)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.[OH-:22].[Na+].Cl>O1CCOCC1>[S:1]1[C:5]([C:6]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][N:9]=[C:8]([OH:22])[N:7]=2)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 60204632HCID 60204632, compound

Product 1

HCID 178517754HCID 178517754, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

4-(Benzo[b]thiophen-2-yl)-2-(methylthio)-5-(trifluoromethyl)pyrimidine (0.45 g, 1.3 mmol) suspended in dioxane (3 mL) was treated with 5 N sodium hydroxide (3 mL) and the reaction heated to 75° C. After stirring overnight, there was still some starting material present in the reaction mixture by LC-MS. An additional 3 mL of 5 N sodium hydroxide was added to the reaction mixture and the temperature was increased to 90° C. After 6 h, the reaction was cooled to room temperature and acidified to pH 4 with 1 N hydrochloric acid. The precipitate that formed was collected by suction filtration, washed well with water and dried in a vacuum oven to give a white solid. Yield=0.31 g. MS (M+H)+ 297.

Workup

  1. temperaturethe temperature was increased to 90° C
  2. waitAfter 6 h
  3. temperaturethe reaction was cooled to room temperature
  4. customThe precipitate that formed
  5. filtrationwas collected by suction filtration
  6. washwashed well with water
  7. customdried in a vacuum oven
  8. customto give a white solid

Sources & evidence

ORD record
ord-9b56cd67012844c8bdafad12c1f3af0c
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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