Phenothiazine → HCID 90386536, compound

HRID 713172Notes

Reaction equation

HRID 713172 reaction equation
[OH-:1].[Na+].[OH:3]O.[CH:5]([C:8]1[CH:13]=[CH:12]C=CC=1)([CH3:7])[CH3:6].[CH:14]1[C:27]2NC3C(=CC=CC=3)SC=2C=CC=1.[CH3:28][CH:29]=[CH:30][C:31](Cl)=[O:32]>C1COCC1>[C:8]([OH:3])(=[O:1])[C:5]([CH3:7])=[CH2:6].[CH:13]([O:1][O:32][C:31]1[CH:14]=[CH:27][CH:28]=[CH:29][CH:30]=1)([CH3:12])[CH3:8]

Participants

6

Reactant 4

HCID 7108Phenothiazine2×HCID 14798Sodium HydroxideHCID 790802-Butenoyl chlorideHCID 21225480HCID 21225480, compound

Product 1

HCID 90386536HCID 90386536, compoundYield 88.21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Drop 100 mL of NaOH solution at a mass percentage of 20% into isopropylbenzene hydrogen peroxide (30.0004 g, 0.2 mol) solution dissolved in THF (20 mL) and added with phenothiazine (0.0199 g, 0.2 mmol), and control the temperature at 0˜15° C. After completing addition, let it react for 60 min to generate a sodium isopropylbenzene peroxide solution. Then drop the methylacryloyl chloride (21.0103 g, 0.2 mol) solution dissolved in THF (20 mL) and added with phenothiazine (0.0198 g, 0.01 mmol), control the temperature at 0˜10° C., and let it react for 3 h after completion of addition. Then extract it with petroleum ether, and wash it with distilled water until a transparent water phase is obtained, separate the oil phase and add anhydrous Na2SO4 to dry it, and distill it at reduced pressure to obtain the product isopropylphenyl peroxide methacrylate, with a total yield of 88.21% at a purity of 98.67%. The structural formula of the product is:

Workup

  1. customat 0˜15° C
  2. additionaddition
  3. customreact for 60 min
  4. customat 0˜10° C.
  5. customreact for 3 h
  6. additionafter completion of addition
  7. extractionThen extract it with petroleum ether
  8. washwash it with distilled water until a transparent water phase
  9. customis obtained
  10. customseparate the oil phase
  11. additionadd anhydrous Na2SO4
  12. customto dry it
  13. distillationdistill it at reduced pressure

Sources & evidence

ORD record
ord-bbace52610364f0c9a13c52899c2b078
Source dataset
uspto-grants-2015_11
Patent number
US09181374B2

Reaction notes

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