Hydrochloric Acid → HCID 23451898, compound

HRID 2174416Notes

Reaction equation

HRID 2174416 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-869ce55676494cc0a280838c45a3f982
Source dataset
uspto-grants-2015_06
Patent number
US09061979B2

Reaction notes

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