Sulfamic Acid → HCID 12769847, compound

HRID 904227Notes

Reaction equation

HRID 904227 reaction equation
S(=O)(=O)(O)N.[CH3:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:21])[CH:19]=[O:20])=[CH:14][CH:13]=1.Cl([O-])=[O:23].[Na+].S([O-])(O)=O.[Na+]>O.C(Cl)(Cl)Cl>[CH3:6][C:7]1[CH:11]=[CH:10][S:9][C:8]=1[C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:21])[C:19]([OH:23])=[O:20])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 23333827HCID 23333827, compoundHCID 23665763Sodium BisulfiteHCID 23668197Sodium Chlorite

Product 1

HCID 12769847HCID 12769847, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

In 20 ml of water was dissolved 3.2 g (0.033 mole) of sulfamic acid. To the solution was added a solution of 5.0 g (0.0217 mole) of 2-[4-(3-methyl-2-thienyl)phenyl]propionaldehyde [obtained in (1)] in 20 ml of chloroform. To the mixture, while maintaining the temperature at 0° to 10° C., was added dropwise with stirring 10 ml of an aqueous solution containing 2.6 g (0.0242 mole) of sodium chlorite (84% pure). After completion of the addition, the mixture was stirred for 10 minutes, admixed with 2.6 g (0.025 mole) of sodium hydrogensulfite, further stirred for 30 minutes, and allowed to stand, upon which the mixture separated into two layers. The organic layer was washed with 20 ml of water and extracted by the addition of 25 ml of 1 N aqueous sodium hydroxide solution. To the alkaline extract layer, which had been admixed with 20 ml of cyclohexane, was added gradually with stirring 5% hydrochloric acid to adjust the pH to 4. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and freed from the solvent by distillation under reduced pressure to obtain an oily substance which was crystallized by the addition of a small quantity of n-hexane to yield 4.8 g (90% yield) of 2-[4-(3-methyl-2-thienyl)phenyl]propionic acid.

Workup

  1. temperatureTo the mixture, while maintaining the temperature at 0° to 10° C.
  2. additionwas added dropwise
  3. additionAfter completion of the addition
  4. stirringfurther stirred for 30 minutes
  5. customseparated into two layers
  6. washThe organic layer was washed with 20 ml of water
  7. extractionextracted by the addition of 25 ml of 1 N aqueous sodium hydroxide solution
  8. extractionTo the alkaline extract layer, which
  9. additionwas added gradually
  10. stirringwith stirring 5% hydrochloric acid
  11. washThe organic layer was washed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationfreed from the solvent by distillation under reduced pressure
  14. customto obtain an oily substance which
  15. customwas crystallized by the addition of a small quantity of n-hexane

Sources & evidence

ORD record
ord-94ba37fb41b4411db6cb02486e1c067b
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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