Hydrochloric Acid → HCID 13417886, compound

HRID 1742795Notes

Reaction equation

HRID 1742795 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].C=O.[C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].C=O.N(CC(O)=O)[CH2:28]C(O)=O.Cl>O>[C:3]([CH2:2][N:1]([CH2:28][C:22]1[CH:23]=[C:18]([NH:17][C:14](=[O:16])[CH3:15])[CH:19]=[CH:20][C:21]=1[OH:24])[CH2:6][C:7]([OH:9])=[O:8])([OH:5])=[O:4]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1983AcetaminophenHCID 8897Iminodiacetic acidHCID 14798Sodium Hydroxide2×HCID 86748091HCID 86748091, compound

Product 1

HCID 13417886HCID 13417886, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
55 °C

Procedure

Deionized water (35.3 g), 35.3 g of 98% iminodiacetic acid (0.25 mole), and 29.9 g of 50% aqueous sodium hydroxide solution were weighed into a round-bottom reaction flask equipped with a water-cooled reflux condenser, mechanical stirrer, thermometer with a temperature controller, and an addition funnel. The mix was heated, with stirring, to a temperature of 55° C. Aqueous 37% formaldehyde solution (21.5 g) was placed in the addition funnel and added to the reaction flask over a 15 minute period. The reaction mixture was heated at 55° C. for approximately 45 minutes, cooled and transferred to an addition funnel. To a round-bottom flask equipped as above was added 38.7 g (0.25 mole) of 98% 4-acetamidophenol, 35.3 g of deionized water, and 12.2 g of 50% aqueous sodium hydroxide solution. The mix was heated, with stirring, to a temperature of approximately 65° C., and the formaldehyde-iminodiacetic acid adduct solution added over a 30 minute period. The reaction mixture was heated at 65° C. for an additional twelve hours and cooled. Concentrated hydrochloric acid (55.5 g) was added and the reaction mixture stirred for one hour. The solution was allowed to stand for several weeks and then the crystalline precipitate filtered, washed with deionized water and dried in a vacuum oven at 65° C. for several hours. Approximately 17.4 g. of solids were recovered. The structure was confirmed by proton NMR. (See Table I.)

Workup

  1. temperaturecooled
  2. temperaturereflux condenser, mechanical stirrer
  3. temperatureThe mix was heated
  4. additionadded to the reaction flask over a 15 minute period
  5. temperatureThe reaction mixture was heated at 55° C. for approximately 45 minutes
  6. temperaturecooled
  7. customtransferred to an addition funnel
  8. customTo a round-bottom flask equipped
  9. temperatureThe mix was heated
  10. stirringwith stirring, to a temperature of approximately 65° C.
  11. temperatureThe reaction mixture was heated at 65° C. for an additional twelve hours
  12. temperaturecooled
  13. stirringthe reaction mixture stirred for one hour
  14. waitto stand for several weeks
  15. filtrationthe crystalline precipitate filtered
  16. washwashed with deionized water
  17. customdried in a vacuum oven at 65° C. for several hours
  18. customof solids were recovered

Sources & evidence

ORD record
ord-b5feb0994aee4e9f999f31197aaab2d9
Source dataset
uspto-grants-1994_08
Patent number
US05342604

Reaction notes

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