Toluene → HCID 3064518, compound

HRID 2118484Notes

Reaction equation

HRID 2118484 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[S:6][C:7]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1.C1(C)C=CC=CC=1.Cl[CH2:32][CH2:33][CH:34]1[O:39][CH2:38][CH2:37][CH2:36][O:35]1>C(N(CC)CC)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[S:6][C:7]3[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:32][CH2:33][CH:34]4[O:39][CH2:38][CH2:37][CH2:36][O:35]4)[CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 833182-(2-Chloroethyl)-1,3-dioxaneHCID 12232379HCID 12232379, compound

Product 1

HCID 3064518HCID 3064518, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2-chloro-7-fluoro-10-piperazino-10,11-dihydro-dibenzo(b,f)thiepin (10.0 g), toluene (60 ml), triethylamine (10 g) and 2-(2-chloroethyl)-1,3-dioxane (15.3 g) is refluxed under stirring for 23 hours. On cooling, the precipitate is filtered off and washed with benzene. The combined filtrates are then washed with water, dried over anhydrous potassium carbonate, filtered with a small amount of active carbon, and evaporated under reduced pressure to dryness. The residue (19.0 g) crystallizes rapidly while standing. Another crystallization from a mixture of benzene (50 ml) and petroleum ether (50 ml) yields 8.5 g (65%) of the desired base, melting at 150.5°-152° C. Repeating the crystallization from the same solvent system does not increase the m.p. any more; the product is analytically pure, and its elemental analysis corresponds to the composition C24H28ClFN2O2S. Neutralization of the base, with maleic acid in a mixture of equal amounts of benzene, acetone and ethanol, provides the neutral maleate C28H32ClFN2O6S, which crystallizes from ethanol and melts in the pure state at 184°-185° C. This salt is only very slightly soluble in water. Neutralization of base with methanesulfonic acid in ethanol gives the monomethanesulfonate C25H32ClFN2O5S2, which crystallizes from ethanol and melts at 201°-203° C. This salt is excellently water-soluble.

Workup

  1. temperatureis refluxed
  2. temperatureOn cooling
  3. filtrationthe precipitate is filtered off
  4. washwashed with benzene
  5. washThe combined filtrates are then washed with water
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered with a small amount of active carbon
  8. customevaporated under reduced pressure to dryness
  9. customThe residue (19.0 g) crystallizes rapidly
  10. customAnother crystallization
  11. additionfrom a mixture of benzene (50 ml) and petroleum ether (50 ml)

Sources & evidence

ORD record
ord-6cc48da40c25402a9a715ac9e72f8e4c
Source dataset
uspto-grants-1987_07
Patent number
US04678788

Reaction notes

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