Methacryloyl chloride → 2-Methoxy-10-(alpha-methyl acryloyl)-phenothiazine

HRID 1288540Notes

Reaction equation

HRID 1288540 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([C:17](=[O:21])[C:18]([CH3:20])=[CH2:19])[C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 13528Methacryloyl chlorideHCID 74490Methyl phenothiazin-2-yl ether

Product 1

HCID 543690422-Methoxy-10-(alpha-methyl acryloyl)-phenothiazineYield 99.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 23 g of 2methoxy-phenothiazine, 21 g of methacryloyl chloride and 120 ml of toluene was refluxed for 3 hours and was then cooled and washed with 250 ml of N sodium hydroxide. The organic phase was decanted and the aqueous phase was washed twice with 50 ml of toluene. The combined organic phases were washed with water, dried over magnesium sulfate, treated with carbon black and evaporated to dryness to obtain 29.6 g of 2-methoxy-10-(α-methyl acryloyl)-phenothiazine melting at 91°-92° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturewas then cooled
  3. washwashed with 250 ml of N sodium hydroxide
  4. customThe organic phase was decanted
  5. washthe aqueous phase was washed twice with 50 ml of toluene
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with carbon black
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-1931f6490d74424b8ff7350420152be2
Source dataset
uspto-grants-1976_10
Patent number
US03988453

Reaction notes

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