p-Toluenesulfonic acid monohydrate → HCID 21265540, compound

HRID 566191Notes

Reaction equation

HRID 566191 reaction equation
[CH2:1]([C:4]1[C:9]([OH:10])=[C:8]([Br:11])[CH:7]=[C:6]([F:12])[C:5]=1[N:13]1[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]1=[O:25])[CH:2]=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Br:11][C:8]1[C:9]2[O:10][CH:2]([CH3:3])[CH2:1][C:4]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[N:15]([CH3:24])[C:14]2=[O:25])=[C:6]([F:12])[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21265517HCID 21265517, compound

Product 1

HCID 21265540HCID 21265540, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-(2-Allyl-4-bromo-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidine-dione (1.50 g) was dissolved in xylene (15 ml). After p-toluenesulfonic acid monohydrate (0.54 g) was added thereto, it was allowed to react under the refluxing condition for 12 hours. After the completion of the reaction, it was extracted with ethyl acetate, washed with an aqueous sodium hydrogen-carbonate solution and water, and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off, and the resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3) to obtain the objective 3-(7-bromo-5-fluoro-2-methyl-2,3-dihydro-benzo[b]furan-4-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (1.46 g).

Workup

  1. customto react under the refluxing condition for 12 hours
  2. customAfter the completion of the reaction, it
  3. extractionwas extracted with ethyl acetate
  4. washwashed with an aqueous sodium hydrogen-carbonate solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off
  7. customthe resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3)

Sources & evidence

ORD record
ord-ab589c5c794f414eb955d3ba1e78ec15
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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