Hydrochloric Acid → HCID 23451898, compound

HRID 1479707Notes

Reaction equation

HRID 1479707 reaction equation
[S-2:1].[K+].[K+].CN(C=O)C.Cl[C:10]1[CH:29]=[CH:28][C:13]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[O:15])=[CH:12][CH:11]=1.Cl>CC1C=CC=CC=1>[C:22]1([C:19]2[CH:20]=[CH:21][C:16]([C:14](=[O:15])[C:13]3[CH:28]=[CH:29][C:10]([SH:1])=[CH:11][CH:12]=3)=[CH:17][CH:18]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 162263Potassium SulfideHCID 702323HCID 702323, compound

Product 1

HCID 23451898HCID 23451898, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

15 g anhydrous potassium sulfide and 100 ml DMF are added into a 250 ml three-neck flask. The solution is heated to 50° C. under stirring, and then 8 g 4-chloro-4′-phenyl benzophenone is added into the solution; the solution is heated to reflux (about 110° C.), and is cooled after 7 h; adding 100 ml methylbenzene, regulating the pH value to 5-6 with diluted hydrochloric acid, and separating the solution; the organic phase is extracted twice with 50 ml NaOH solution having a content of 5%, and the aqueous phases are mixed; the obtained aqueous phase is put into a 250 ml three-neck flask, and nitrogen is supplied to blow for 30 min, then 15% hydrochloric acid is dropped into the aqueous solution while agitating to regulate the pH value to 5-6, and light yellow solid precipitate; filtering to obtain a light yellow solid, and the weight after drying at a reduced pressure is 5.0 g, the purity is 99.11%, the yield is 63%, the melting point is 173˜176.7° C., and 1H-NMR data (solvent CDCl3): δ3.654 ppm, s, 1H; δ7.432, 7.370 ppm, d, 2H; δ7.413, 7.436 ppm, d, 1H; δ7.466, 7.491, 7.515 ppm, t, 2H; δ7.641, 7.665 ppm, d, 2H; δ7.695, 7.719 ppm, 7.743, t, 4H; δ7.850, 7.874 ppm, d, 2H.

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux (about 110° C.)
  3. temperatureis cooled after 7 h
  4. customseparating the solution
  5. extractionthe organic phase is extracted twice with 50 ml NaOH solution
  6. additionthe aqueous phases are mixed
  7. customthe obtained aqueous phase is put into a 250 ml three-neck flask
  8. addition15% hydrochloric acid is dropped into the aqueous solution
  9. stirringwhile agitating
  10. filtrationfiltering
  11. customto obtain a light yellow solid
  12. customthe weight after drying at a reduced pressure

Sources & evidence

ORD record
ord-71c0c6e2d79a4cf5a66153162b776f99
Source dataset
uspto-grants-2016_08
Patent number
US09409861B2

Reaction notes

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