Dichloromethane → Sodium Carbonate

HRID 1647378Notes

Reaction equation

HRID 1647378 reaction equation
ClCCl.[C:4](=[O:7])([O-:6])[O-:5].[Na+:8].[Na+].[Fe-4:10]([C:21]#[N:22])([C:19]#[N:20])([C:17]#[N:18])([C:15]#[N:16])([C:13]#[N:14])[C:11]#[N:12].[K+:23].[K+].[K+].[K+].[Fe-3:27]([C:38]#[N:39])([C:36]#[N:37])([C:34]#[N:35])([C:32]#[N:33])([C:30]#[N:31])[C:28]#[N:29].[K+].[K+].[K+].[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>O>[C:4](=[O:5])([O-:7])[O-:6].[Na+:8].[Na+:8].[Fe-4:10]([C:19]#[N:20])([C:15]#[N:16])([C:11]#[N:12])([C:13]#[N:14])([C:17]#[N:18])[C:21]#[N:22].[K+:23].[K+:23].[K+:23].[K+:23].[Fe-3:27]([C:36]#[N:37])([C:32]#[N:33])([C:28]#[N:29])([C:30]#[N:31])([C:34]#[N:35])[C:38]#[N:39].[K+:23].[K+:23].[K+:23]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 178511488HCID 178511488, compound4×HCID 178511490HCID 178511490, compound

Product 3

HCID 10340Sodium CarbonateHCID 178511488HCID 178511488, compoundHCID 178511492HCID 178511492, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Coupler F (5.65 g, 20.98 mmol) was stirred vigorously for 15 minutes with 300 ml dichloromethane. Blocked developer 1-n-butyl-3-(4'-N,N-diethylamino)phenyl urea (5.194 g 19.72 mmol) was ground to a fine powder in a mortar and added to the reaction mixture. A solution of sodium carbonate (40 g, 378.94 mmol) in 800 ml of water was prepared. A solution of potassium ferrocyanide (15.08 g, 35.70 mmol) and potassium ferricyanide (1.32 g, 4.0 mmol) in 20.0 ml water was prepared. The sodium carbonate solution was added to the reaction mixture and the dropwise addition of the potassium ferrocyanide/potassium ferricyanide solution was begun immediately and continued over a 15 minute period. The mixture was stirred an additional 15 minutes and potassium ferricyanide (1.32 g, 4.0 mmol) was added. The mixture was stirred an additional 20 minutes and potassium ferricyanide (2.6 g, 8.0 mmol) was added. The mixture was stirred an additional 25 minutes and potassium ferricyanide (2.6 g, 8.0 mmol) was added. The mixture was stirred an additional 25 minutes and potassium ferricyanide (2.6 g, 8.0 mmol) was again added. The aqueous phase was separated and the organic phase was washed twice with saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The crude product residue was purified by chromatography on a Waters Prep 500 HPLC using a 4:1 dichloromethane/ethyl acetate solvent system to give yellow leuco dye G contaminated with some 3-butyl-1-[4'-N,N-diethylamino-2'-(2-benzoyl-o-methoxyacetanilidyl)]phenyl urea.

Workup

  1. additionadded to the reaction mixture
  2. stirringThe mixture was stirred an additional 20 minutes
  3. stirringThe mixture was stirred an additional 25 minutes
  4. stirringThe mixture was stirred an additional 25 minutes
  5. customThe aqueous phase was separated
  6. washthe organic phase was washed twice with saturated sodium chloride solution
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo
  10. customThe crude product residue was purified by chromatography on a Waters Prep 500 HPLC
  11. customto give yellow leuco dye G

Sources & evidence

ORD record
ord-5fc118b39a484b3e935e8054c16f277b
Source dataset
uspto-grants-1995_07
Patent number
US05432041

Reaction notes

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