Water → HCID 19966724, compound

HRID 976220Notes

Reaction equation

HRID 976220 reaction equation
C([Li])CCC.[Cl-].[CH3:7][O:8][NH3+:9].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=[C:14](S(C)(=O)=O)[N:13]=1.O>CCCCCC.O1CCCC1>[CH3:7][O:8][NH:9][C:14]1[N:13]=[C:12]([O:11][CH3:10])[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[N:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11639O-methylhydroxylammonium chlorideHCID 14280157HCID 14280157, compoundHCID 178418339Butyllithium

Product 1

HCID 19966724HCID 19966724, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

66.6 g of a 1.6 molar solution of n-butyllithium (0.156 mol) in n-hexane were added dropwise to a solution of 6.5 g of O-methylhydroxylammonium chloride (78 mmol) in 200 ml of tetrahydrofuran at -10° C. Stirring was carried out for 10 minutes at -10° C., and 20 g of 4-methoxy-2-methylsulfonyl-6-trifluoromethylpyrimidine (78 mmol) were added to the cloudy solution. Stirring was carried out for 1 hour at 25° C., the reaction batch was introduced into 200 ml of water, and the organic phase was separated off, washed with water and dried. Removal of the solvent gave an oily, slightly impure product, which could be crystallized in pentane at -78° C. 7.5 g of the product (43% of theory) were obtained as colorless crystals of melting point. 44°-46° C.

Workup

  1. stirringStirring
  2. waitwas carried out for 1 hour at 25° C.
  3. customthe organic phase was separated off
  4. washwashed with water
  5. customdried
  6. customRemoval of the solvent
  7. customgave an oily, slightly impure product, which
  8. customcould be crystallized in pentane at -78° C

Sources & evidence

ORD record
ord-9ae80900bb0f408e837ff93d13457e49
Source dataset
uspto-grants-1997_03
Patent number
US05612286

Reaction notes

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