Chloroform → HCID 86752880, compound

HRID 965299Notes

Reaction equation

HRID 965299 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-chloroethyl)-5-fluoro-1H-indole-2,3-dione (2.27 g), propanedithiol (1.1 ml) in chloroform was added dropwise to a stirred solution of boron trifluoride etherate (1.2 ml) in acetic acid (2.2 ml) and chloroform (10 ml) which was maintained at a gentle reflux throughout the addition. After 1.5 h reaction time 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 and triturated with ether to give 1-(2-chloroethyl)-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 1.5 h reaction time 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
  9. customtriturated with ether

Sources & evidence

ORD record
ord-e0381262707a4791bdab4d23b8d86c40
Source dataset
uspto-grants-1998_06
Patent number
US05773448

Reaction notes

Loading…