Dimethyl Sulfate → HCID 86607605, compound

HRID 2357522Notes

Reaction equation

HRID 2357522 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[C:14]([I:15])[C:9]=2[O:8][N:7]=1)=[O:4].S(OC)(O[CH3:23])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:18][C:2]([F:17])([F:1])[C:3]([N:5]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[C:14]([I:15])[C:9]=2[O:8][N:7]=1)[CH3:23])=[O:4]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 86607604HCID 86607604, compound

Product 1

HCID 86607605HCID 86607605, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To 2,2,2-trifluoro-N-(7-iodo-6-methylbenzo[d]isoxazol-3-yl)acetamide in acetone (5.0 mL) at RT was added dimethyl sulfate (766 mg, 6.07 mmol) and potassium carbonate (1.40 g, 10.12 mmol). The mixture was heated at 50° C. in an oil bath for 5 h, then cooled to RT, filtered through a pad of Celite and rinsed with additional acetone (2×5 mL). The filtrate was concentrated to dryness to provide 2,2,2-trifluoro-N-(7-iodo-6-methylbenzo[d]isoxazol-3-yl)-N-methylacetamide. MS (ESI, pos. ion) m/z: 385.0 (M+1).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through a pad of Celite
  3. washrinsed with additional acetone (2×5 mL)
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-af5377e77b264c2bb55d00464bdcf9fc
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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