Formic Acid → HCID 15918615, compound

HRID 1906532Notes

Reaction equation

HRID 1906532 reaction equation
CNC1C=CC2N=C3C(SC=2C=1)=CC(=[N+](C)C)C=C3.[Cl-].[Cl-].[CH3:22][N:23]([CH3:40])[C:24]1[CH:25]=[C:26]2[C:35](=[CH:36][CH:37]=1)[N:34]=[C:33]1[C:28]([CH:29]=[C:30]([NH:38][CH3:39])[CH:31]=[CH:32]1)=[S+:27]2.[CH:41]([OH:43])=O.N1C=CC=CC=1.[CH:50]([OH:53])(C)C>[Zn].CCCCCC>[CH3:22][N:23]([CH3:40])[C:24]1[CH:25]=[C:26]2[C:35](=[CH:36][CH:37]=1)[N:34]([CH:50]=[O:53])[C:33]1[CH:32]=[CH:31][C:30]([N:38]([CH:41]=[O:43])[CH3:39])=[CH:29][C:28]=1[S:27]2

Participants

8

Reactant 5

HCID 284Formic AcidHCID 1049PyridineHCID 3776IsopropanolHCID 68275N,N-Dimethyl-7-(methylamino)-3H-phenothiazin-3-iminium chlorideHCID 178482078HCID 178482078, compound

Product 1

HCID 15918615HCID 15918615, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8058HexaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 10.0 g of Azure B (Aldrich) 7-(dimethylamino)-3-(methylamino)phenothiazin-5-ium chloride, 75.0 ml of 90 percent formic acid, 5.0 g of zinc dust and 5.0 ml of pyridine was maintained at approximately 90° C. for approximately three hours. The reaction mixture was cooled to room temperature and filtered, saving the filtrate. The filter cake was washed twice, each time with 50.0 ml of acetone, and the washes combined with the filtrate. The combined filtrate and washes was poured into ice water with stirring. The resulting solution was extracted with toluene. The toluene solution was separated, treated with decolorizing carbon, filtered and the resulting solution was evaporated under reduced pressure to obtain a gummy residue. The gummy residue was titurated with a 1:1 (V:V) mixture of isopropyl alcohol and hexane. The solid which formed was collected by filtration and dried to obtain 0.14 g of 7-(dimethylamino)-3-(N-formyl-N-methylamino)-10-formylphenothiazine (Formula II: R=R1 =R5 =H; R2 =R3 =R4 =CH3), an off-white-colored powder which melted at 139° to 143° C. A significant infrared maximum appeared at 1685 cm-1 (C=O; s). A paper treated with an ink formulation of the product produced a black-colored image when traced with an applied voltage stylus.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe filter cake was washed twice
  4. additionThe combined filtrate and washes was poured into ice water
  5. extractionThe resulting solution was extracted with toluene
  6. customThe toluene solution was separated
  7. additiontreated with decolorizing carbon
  8. filtrationfiltered
  9. customthe resulting solution was evaporated under reduced pressure
  10. customto obtain a gummy residue
  11. customThe solid which formed
  12. filtrationwas collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-dceb7a14c9d44378b2a0756813b9a09e
Source dataset
uspto-grants-1987_03
Patent number
US04652643

Reaction notes

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