Water → HCID 20458352, compound

HRID 544661Notes

Reaction equation

HRID 544661 reaction equation
C[O:2][CH:3](OC)[CH2:4][S:5]([C:7]1[S:8][C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:11]=1)=[O:6].S(=O)(=O)(O)O.O>C(O)(=O)C.C(Cl)Cl>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:11]=[C:7]([S:5]([CH2:4][CH:3]=[O:2])=[O:6])[S:8][C:9]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 20458355HCID 20458355, compound

Product 1

HCID 20458352HCID 20458352, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

5.75 g of 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylsulphinyl]-acetaldehyde-dimethylacetal are dissolved in 5 ml of acetic acid. Then, while stirring, 30 ml of a mixture of 2 parts acetic acid, 1 part sulphuric acid and 1 part water are added dropwise over a period of 5 minutes. The mixture is stirred at room temperature for 30 minutes, diluted with 100 ml of methylene chloride and poured into 200 ml of ice-water. The organic layer is removed and washed with 200 ml of ice-water. The aqueous phase is extracted by shaking three times with 50 ml of methylene chloride each time. The organic phases are combined, dried over magnesium sulphate and concentrated to dryness by evaporation. The crude product is dissolved in 200 ml of methylene chloride and stirred with 5 g of silica gel. The mixture is filtered, concentrated to dryness by evaporation and dried under reduced pressure. 2-[4,5-bis-(p-methoxyphenyl)-thiazol-2-ylsulphinyl]-acetaldehyde is obtained in the form of a highly viscous oil, IR-spectrum: νC=O =1720 cm-1, νS=O =1080 cm-1 (CCl4).

Workup

  1. stirringThe mixture is stirred at room temperature for 30 minutes
  2. customThe organic layer is removed
  3. washwashed with 200 ml of ice-water
  4. extractionThe aqueous phase is extracted
  5. stirringby shaking three times with 50 ml of methylene chloride each time
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness by evaporation
  8. dissolutionThe crude product is dissolved in 200 ml of methylene chloride
  9. stirringstirred with 5 g of silica gel
  10. filtrationThe mixture is filtered
  11. concentrationconcentrated to dryness by evaporation
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-00d41836222b4b7cbc6c98fb717bdb6c
Source dataset
uspto-grants-1984_05
Patent number
US04451471

Reaction notes

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