Hydrochloric Acid → HCID 19876588, compound

HRID 1885974Notes

Reaction equation

HRID 1885974 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:18])[C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[H-].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.Cl.[Cl-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])=[C:6]([NH:18][C:25]2[N:26]=[C:27]([O:29][CH3:30])[CH:28]=[C:23]([O:22][CH3:21])[N:24]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 19876601HCID 19876601, compound

Product 1

HCID 19876588HCID 19876588, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a solution of 5.2 grams (0.020 mole) of phenylmethyl 6-chloroanthranilate in 150 mL of tetrahydrofuran was stirred, and 0.8 gram (0.02 mole) of 60% sodium hydride in mineral was added in one portion. Upon completion of addition, the reaction mixture was stirred for 5 minutes, and the reaction mixture temperature was slowly brought to 50° C. After this time 4.3 grams (0.020 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine (prepared as in Example 1, Steps A-C) was added in one portion. Upon completion of - addition, the reaction mixture was warmed to reflux where it was stirred for about 18 hours. The reaction mixture was cooled to ambient temperature and was poured into a solution of 50 mL of 3N hydrochloric acid and 200 mL of an aqueous solution saturated with sodium chloride. The mixture was extracted with three 250 mL portions of diethyl ether. The combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was adsorbed onto silica gel and was subjected to column chromatography on silica gel. Elution was accomplished with 20% ethyl acetate in hexane. The appropriate fractions were combined and concentrated under reduced pressure to yield 4.0 grams of phenylmethyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-ylamino)benzoate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. customwas slowly brought to 50° C
  3. additionUpon completion of - addition
  4. temperaturethe reaction mixture was warmed
  5. temperatureto reflux where it
  6. stirringwas stirred for about 18 hours
  7. extractionThe mixture was extracted with three 250 mL portions of diethyl ether
  8. washThe combined extracts were washed with one 250 mL portion of an aqueous solution saturated with sodium chloride
  9. dry with materialThe organic layer was dried with magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  12. washElution
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ab4933148934a9d933e752f0677c54a
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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