Phenothiazine → HCID 86747811, compound

HRID 1033033Notes

Reaction equation

HRID 1033033 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([NH:6][C:7](=[O:11])[CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[CH3:14].[H-].[Na+].[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].C1C2NC3C(=CC=CC=3)SC=2C=CC=1>O1CCCC1.N1C=CN=C1>[C:9]([C:8](=[C:17]([OH:21])[C:18]([CH3:20])=[CH2:19])[C:7]([NH:6][C:5]1[CH:12]=[CH:13][C:2]([Br:1])=[C:3]([CH3:14])[CH:4]=1)=[O:11])#[N:10]

Participants

7

Reactant 4

HCID 7108PhenothiazineHCID 13528Methacryloyl chlorideHCID 24758Sodium hydrideHCID 10538801HCID 10538801, compound

Product 1

HCID 86747811HCID 86747811, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 795ImidazoleCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.3 g of 4'-bromo-3'-methyl-cyanoacetanilide (0.025 mole) in 200 ml of dry tetrahydrofuran was stirred under nitrogen during the addition of 0.02 g of imidazole as a catalyst and 1.85 g (0.0625 mole) of sodium hydride 80% oil dispersion. The suspension was stirred at room temperature for 1 hour, then was cooled to -78° C. 2.95 ml (0.03 mole) of methacryloyl chloride freshly distilled from phenothiazine were added dropwise and the mixture was warmed to -20° C. over 90 minutes. The mixture was poured onto dilute hydrochloric acid/ice, and filtered. The solid was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to obtain 8.0 g (99.7%) of the title compound as colorless crystals.

Workup

  1. temperaturewas cooled to -78° C
  2. additionwere added dropwise
  3. temperaturethe mixture was warmed to -20° C. over 90 minutes
  4. filtrationfiltered
  5. dissolutionThe solid was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2f00a35bf7be43929ae2675186dfe43b
Source dataset
uspto-grants-1994_05
Patent number
US05308865

Reaction notes

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