Sodium Bicarbonate → HCID 18957084, compound

HRID 1885357Notes

Reaction equation

HRID 1885357 reaction equation
F[B-](F)(F)F.C([O+:8]([CH2:11][CH3:12])[CH2:9][CH3:10])C.[Cl:13][C:14]1[CH:22]=C2[C:17]([CH2:18][NH:19]C2=O)=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:11]([O:8][C:9]1[C:10]2[C:17](=[CH:16][CH:15]=[C:14]([Cl:13])[CH:22]=2)[CH2:18][N:19]=1)[CH3:12]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723982Triethyloxonium tetrafluoroborateHCID 124964756-Chloro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 18957084HCID 18957084, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 151 g of triethyloxonium tetrafluoroborate in 3200 ml of methylene chloride was stirred under argon at room temperature for 3.5 hours after the addition of 106.6 g of 6-chloro-2,3-dihydro-1H-isoindol-1-one. The mixture was then treated within 40 minutes with 1.28 l of saturated sodium hydrogen carbonate solution, the organic phase was separated and washed with 1.28 l of water. After drying over sodium sulphate the organic phase was filtered and evaporated. The residue was taken up in 1.3 l of diethyl ether, whereupon it was stirred at room temperature for about 30 minutes. After removing insoluble material by filtration the filtrate was evaporated. There was obtained 110.5 g of 1-ethoxy-6-chloro-3H-isoindole with a m.p. of 64°-66°.

Workup

  1. customthe organic phase was separated
  2. washwashed with 1.28 l of water
  3. dry with materialAfter drying over sodium sulphate the organic phase
  4. filtrationwas filtered
  5. customevaporated
  6. customAfter removing insoluble material
  7. filtrationby filtration the filtrate
  8. customwas evaporated

Sources & evidence

ORD record
ord-77472a446eb3496abc51dde50aaa3f4c
Source dataset
uspto-grants-1992_09
Patent number
US05143912

Reaction notes

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