Sodium Carbonate → HCID 18921413, compound

HRID 1289364Notes

Reaction equation

HRID 1289364 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:8](=[O:20])(=[O:19])[CH2:7][C:6]=2[C:21]=1[N+:22]([O-])=O.Cl[Sn]Cl.O.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[F:1][C:2]1[C:21]([NH2:22])=[C:6]2[CH2:7][S:8](=[O:20])(=[O:19])[N:9]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 43835034Tin dichloride dihydrateHCID 54418653HCID 54418653, compound

Product 1

HCID 18921413HCID 18921413, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 5-fluoro-1,3-dihydro-1-[(4-methoxyphenyl)methyl]-4-nitro-2,1-benzisothiazole 2,2-dioxide (1.54 g, 4.37 mmol) and SnCl2.H2O (4.93 g, 21.9 mmol) in ethyl acetate (200 mL) was heated at reflux for 3 h. Then the reaction mixture was cooled, diluted with ethyl acetate (200 mL) and solid Na2CO3 (15 g) was added. The resulting mixture was vigorously stirred for 12 h and filtered through a pad of diatomaceous earth (Celite®). The filtrate was concentrated and the residue was subjected to flash chromatography to give 1.35 g of the title compound of Step C as brown solid melting at 154°-157° C. 1H NMR (CDCl3, 400 MHz): δ7.33 (d,2H), 6.87 (d,2H), 6.82 (dd,1H, J=11.3 and 8.75 Hz), 5.91 (dd,1H, J=8.5 and 3.5 Hz), 4.65 (s,2H), 4.22 (s,2H), 3.79 (s,3H), 3.75 (br s,2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThen the reaction mixture was cooled
  4. additionwas added
  5. filtrationfiltered through a pad of diatomaceous earth (Celite®)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f67454ebd15a496783c4b031454b4b48
Source dataset
uspto-grants-1998_05
Patent number
US05750471

Reaction notes

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