Methyl iodide → HCID 22404778, compound

HRID 440705Notes

Reaction equation

HRID 440705 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=[O:24])=[CH:4][CH:3]=1.CI.C(=O)([O-])[O-].[K+].[K+].[NH2:33]OS(C1C(C)=CC(C)=CC=1C)(=O)=O>O1CCCC1.O>[NH2:33][N:15]1[C:16]([C:20]([F:23])([F:22])[F:21])=[CH:17][C:18](=[O:19])[N:13]([C:5]2[C:6]3[O:10][C:9]([CH3:11])([CH3:12])[CH2:8][C:7]=3[C:2]([Cl:1])=[CH:3][CH:4]=2)[C:14]1=[O:24]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium Carbonate2×HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 22404807HCID 22404807, compound

Product 1

HCID 22404778HCID 22404778, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.0 gram (0.003 mole) of 3-(4-chloro-2,3-dihydro-2,2-dimethylbenzofuran-7-yl)-6-trifluoromethyluracil (prepared in a manner analogous to that of Example 1, Step G, except that methyl iodide and potassium carbonate were not used) in 30 mL of tetrahydrofuran was stirred, and 0.5 gram (0.003 mole) of potassium carbonate, then 0.7 gram (0.003 mole) of 1-aminooxysulfonyl-2,4,6-trimethylbenzene were added. Upon completion of the addition, the reaction mixture was stirred for one hour and then diluted with water and extracted with three portions of ethyl acetate. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with 1:4 ethyl acetate:heptane as the eluant. The product-containing fractions were combined and concentrated, yielding 1.0 gram of 1-amino-3-(4-chloro-2,3-dihydro-2,2-dimethylbenzofuran- 7-yl)-6-trifluoromethyluracil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. stirringthe reaction mixture was stirred for one hour
  3. extractionextracted with three portions of ethyl acetate
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c3065e41e1694e8e811004632d0e1330
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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