Dichloromethane → HCID 9928555, compound

HRID 1265179Notes

Reaction equation

HRID 1265179 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]2[CH2:18][S:19][CH2:20][C:15]2=[N:14]1.C(Cl)Cl.C([O-])([O-])=[O:25].[Na+].[Na+]>>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[CH:17]=[C:16]2[CH2:18][S:19](=[O:25])[CH2:20][C:15]2=[N:14]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 9819252HCID 9819252, compound

Product 1

HCID 9928555HCID 9928555, compoundYield 60%

Conditions

Temperature
-30 °C

Procedure

To a solution of compound (3) (41 mg, 0.11 mmol) in CH2Cl2 (3 mL) m-CPBA (31.3 mg, 0.13 mmol) was added at −78° C. under N2. After 30 min. the reaction mixture was allowed to warm to −30° C. and stirred at −30° C. until the starting material disappeared completely. Aqueous Na2CO3 (10 mL) was then added and the organic phase was separated. The organic layer was washed with aq. Na2CO3 (10×4 mL), dried, concentrated to obtain a solid which was purified by flash chromatography on silica (20% EtOAc:hexane) to obtain the title compound (60%). 1H NMR (CDCl3) δ 7.78 (s, 2H), 7.45 (s, 1H), 7.53 (m, 2H), 4.01 (d, J=7.8 Hz, 1H), 3.88 (d, 7.8 Hz, 1H); MS (M+) 355.

Workup

  1. customthe organic phase was separated
  2. washThe organic layer was washed with aq. Na2CO3 (10×4 mL)
  3. customdried
  4. concentrationconcentrated
  5. customto obtain a solid which
  6. customwas purified by flash chromatography on silica (20% EtOAc:hexane)

Sources & evidence

ORD record
ord-677a893faa98493fae4f1a032d9856ff
Source dataset
uspto-grants-2003_04
Patent number
US06545033B1

Reaction notes

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