Chloroform → HCID 86752880, compound

HRID 1276330Notes

Reaction equation

HRID 1276330 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[C:12]2C(=C[C:9]([F:13])=[CH:10][CH:11]=2)C(=O)[C:5]1=[O:15].[CH:16]([SH:20])([SH:19])[CH2:17][CH3:18].B(F)(F)F.CCO[CH2:28][CH3:29].[CH:30](Cl)(Cl)Cl>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][N:4]1[C:12]2[C:17](=[CH:18][C:9]([F:13])=[CH:10][CH:11]=2)[C:16]2([S:20][CH2:29][CH2:28][CH2:30][S:19]2)[C:5]1=[O:15]

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 8000Boron trifluoride etherateHCID 64285461,1-PropanedithiolHCID 11770201HCID 11770201, compound

Product 1

HCID 86752880HCID 86752880, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(2-chloro-1-ethyl)-5-fluoro-1H-indole-2,3-dione, propanedithiol (1.2 equvalents) in chloroform was added dropwise to a stirred solution of boron trifluoride etherate in acetic acid and chloroform which was maintained at a gentle reflux throughout the addition. After 6 hours' reaction the mixture was cooled, washed with water and sodium hydrogen carbonate solution, dried (MgSO4) and filtered through a pad of flash silica using chloroform as eluent. The combined fractions were evaporated under reduced pressure to give 1-(2-chloro-1-ethyl)-1,3-dihydro-5-fluoro-2-oxo-2H-indole-3-spiro-2'-1,3 dithiane.

Workup

  1. temperaturewas maintained at
  2. temperaturea gentle reflux throughout the addition
  3. customAfter 6 hours' reaction the mixture
  4. temperaturewas cooled
  5. washwashed with water and sodium hydrogen carbonate solution
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a pad of flash silica
  8. customThe combined fractions were evaporated under reduced pressure

Sources & evidence

ORD record
ord-65cf89e2a03f48238eaa5e1d33764078
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

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