Trisodium citrate → HCID 54074187, compound

HRID 1274521Notes

Reaction equation

HRID 1274521 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].Br[CH2:14][C:15]([OH:17])=O.P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)Cl.C([O-])(=O)C[C:29]([CH2:34][C:35]([O-:37])=O)([C:31]([O-:33])=O)O.[Na+].[Na+].[Na+]>[Fe](Cl)(Cl)Cl.C(Cl)(Cl)Cl>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]2[C:35](=[O:37])[C:34](=[C:29]3[C:31](=[O:33])[C:7]4[CH:8]=[CH:9][C:4]([N:3]([CH2:11][CH3:12])[CH2:1][CH3:2])=[CH:14][C:15]=4[O:17]3)[O:10][C:6]=2[CH:5]=1)[CH3:12]

Participants

8

Reactant 5

HCID 6224Trisodium citrateHCID 6227Bromoacetic AcidHCID 70623-(Diethylamino)phenolHCID 24387Phosphorus trichlorideHCID 24813Phosphorus oxychloride

Product 1

HCID 54074187HCID 54074187, compound

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6212ChloroformSolvent

Procedure

10.0 g (60.5 mmol) of 3-diethylaminophenol are mixed with 12.5 g (90.1 mmol) of bromoacetic acid at a reaction temperature of 60° C., with exclusion of moisture and vigorous stirring with a precision glass stirrer. 7.0 g (46 mmol) of phosphoryl chloride, 6.3 g (46 mmol) of phosphorus trichloride and 24.6 g (152 mmol) of anhydrous iron trichloride are added. After a reaction time of 24 hours, 3 parts of ice are added to the dark violet mixture and the solid mixture is dissolved with cautious heating and stirring. After addition of sodium citrate (as a complexing agent for Fe3+ -ions), the mixture is extracted by shaking three times with 80 ml of chloroform each time. The dark red organic phase is dried over MgSO4. After the solvent has been stripped off on a rotary evaporator, 55.66 g of dark violet, highly viscous crude product are obtained. 0.7 g of crude product are worked up by column chromatography over silica gel using chloroform as the mobile phase. The trans colorant isomer can be separated off as a red-violet fraction in the first runnings. After the solvent has been stripped off on a rotary evaporator, the resulting dark red solid is dried under an oil pump vacuum at 95° C. for 7 hours.

Workup

  1. additionAfter a reaction time of 24 hours, 3 parts of ice are added to the dark violet mixture
  2. dissolutionthe solid mixture is dissolved
  3. temperaturewith cautious heating
  4. stirringstirring
  5. extractionis extracted
  6. stirringby shaking three times with 80 ml of chloroform each time
  7. dry with materialThe dark red organic phase is dried over MgSO4
  8. customAfter the solvent has been stripped off on a rotary evaporator, 55.66 g of dark violet, highly viscous crude product
  9. customare obtained
  10. customThe trans colorant isomer can be separated off as a red-violet fraction in the first runnings
  11. customAfter the solvent has been stripped off on a rotary evaporator
  12. customthe resulting dark red solid is dried under an oil pump vacuum at 95° C. for 7 hours

Sources & evidence

ORD record
ord-944ce0a8c1f84aec91cababd474eaac1
Source dataset
uspto-grants-2000_12
Patent number
US06156914

Reaction notes

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