Water → HCID 70453742, compound

HRID 364218Notes

Reaction equation

HRID 364218 reaction equation
[Cl-].[NH2:2][C:3]1[C:16]2[C:7](=[O+:8][C:9]3[C:14]([N:15]=2)=[CH:13][C:12]([CH3:17])=[C:11]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:10]=3)[CH:6]=[C:5]([NH2:23])[CH:4]=1.[C:24]([O:27]C(=O)C)(=O)[CH3:25].[N:31]1C=CC=C[CH:32]=1.O.[C:38]1(C)C=CC=CC=1>[Zn]>[CH3:38][N:2]1[C:3]2[C:16]3[NH:15][C:14]4[CH:13]=[C:12]([CH3:17])[C:11]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][C:9]=4[O:8][C:7]=3[CH:6]=[C:5]([NH:23][C:24](=[O:27])[CH3:25])[C:4]=2[N:31]=[CH:32]1

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 178463792HCID 178463792, compound

Product 1

HCID 70453742HCID 70453742, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A mixture of 10.0 g of 1,3-diamino-7-diethylamino-8-methylphenoxazin-5-ium chloride (Brilliant Cresyl Blue, Eastman Kodak), 50.0 ml of acetic anhydride, 10.0 g of zinc dust and 10.0 ml of pyridine was maintained at 85° to 90° C. for approximately one hour. After cooling to room temperature, the reaction mixture was poured into a mixture of water and toluene and the resulting water layer was separated and discarded. The toluene solution was washed twice, first with water and then with saturated sodium chloride solution. The toluene was removed by evaporation at reduced pressure. The resulting residue was recrystallized from isopropanol and the solid obtained was recrystallized from ethanol to obtain 0.2 g of 1,9-dimethyl-4-acetamido-8-diethylaminoimidazophenoxazine (Formula I: R=R3 =CH3 ; R1 =R2 =C2H5), a white solid which melted at 217° to 218° C. A significant infrared maximum appeared at 1660 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Paper coated with an ink formulation of the product produced a purple-colored image when contacted with an applied voltage stylus.

Workup

  1. temperaturewas maintained at 85° to 90° C. for approximately one hour
  2. customthe resulting water layer was separated
  3. washThe toluene solution was washed twice, first with water
  4. customThe toluene was removed by evaporation at reduced pressure
  5. customThe resulting residue was recrystallized from isopropanol
  6. customthe solid obtained
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-9d587e728b1a43d29ac36a6e7dae5c2d
Source dataset
uspto-grants-1986_08
Patent number
US04604462

Reaction notes

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