Hydrochloric Acid → HCID 780872, compound

HRID 863660Notes

Reaction equation

HRID 863660 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>O>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([N:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8897Iminodiacetic acidHCID 14798Sodium Hydroxide

Product 1

HCID 780872HCID 780872, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Iminodiacetic acid (200 g, 1.50 mol) was dissolved in water (3 L) and sodium hydroxide (180 g, 4.5 mol) was added in small portions with stirring. After stirring for 15 minutes, p-toluenesulfonyl chloride (286.5 g, 1.5 mol) was added in small portions. The reaction mixture was heated to 80° C. for one hour, giving a clear solution. At the end of this time, the reaction solution was cooled in an ice bath to 10°--15° C., and concentrated HCl (110 ml) was added, precipitating the product as a white solid. This solid was filtered and washed with cold water, then dried in a vacuum oven at 55° C., giving 207.7 g (0.723 mol, 48.2% yield): mp 195°-196° C . (lit.* mp 191° C.); 1H NMR (DMSO-d6, 300 MHz) δ 2.38 (s, 3H), 3.66 (s, 4H), 7.39 (d, J=8.7 Hz, 2H), 7.65 (d, J=8.1 Hz); 13C NMR (DMSO-d6, 75 MHz) δ 20.90, 53.98, 126.55, 129.79, 136.70, 143.17, 171.77.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customgiving a clear solution
  3. temperatureAt the end of this time, the reaction solution was cooled in an ice bath to 10°--15° C.
  4. customprecipitating the product as a white solid
  5. filtrationThis solid was filtered
  6. washwashed with cold water
  7. customdried in a vacuum oven at 55° C.
  8. customgiving 207.7 g (0.723 mol, 48.2% yield)

Sources & evidence

ORD record
ord-b1cc119abfb2401ba7c5d25f8c45d585
Source dataset
uspto-grants-1998_02
Patent number
US05721361

Reaction notes

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