Sodium Hydroxide → HCID 59533864, compound

HRID 221221Notes

Reaction equation

HRID 221221 reaction equation
[CH:1]1(/[CH:6]=[C:7](\[C:13]2[CH:26]=[CH:25][C:24]3[S:23](=[O:28])(=[O:27])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:29])[C:15]=3[CH:14]=2)/[C:8]([O:10]CC)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1(/[CH:6]=[C:7](\[C:13]2[CH:26]=[CH:25][C:24]3[S:23](=[O:28])(=[O:27])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:29])[C:15]=3[CH:14]=2)/[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59533862HCID 59533862, compound

Product 1

HCID 59533864HCID 59533864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.58 g of ethyl(E)-3-cyclopentyl-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acrylate are dissolved in 130 ml of methanol, and 13.44 ml of 2 M NaOH solution are added. The reaction mixture is heated at the boil under reflux for two hours. The methanol is removed under reduced pressure, and the reaction mixture is adjusted to pH 4 by addition of 2N hydrochloric acid. The precipitated solid is filtered off with suction and dried under high vacuum. This gives 1.46 g of (E)-3-cyclopentyl-2-(10-methyl-5,5-dioxo-5,10-dihydrophenothiazin-2-yl)acrylic acid.

Workup

  1. temperatureThe reaction mixture is heated at the boil
  2. temperatureunder reflux for two hours
  3. customThe methanol is removed under reduced pressure
  4. additionthe reaction mixture is adjusted to pH 4 by addition of 2N hydrochloric acid
  5. filtrationThe precipitated solid is filtered off with suction
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-254708f121ef476192a42798afa5c2bb
Source dataset
uspto-grants-2012_06
Patent number
US08207146B2

Reaction notes

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