Benzenesulfonyl chloride → HCID 3113398, compound

HRID 1906375Notes

Reaction equation

HRID 1906375 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].[OH-].[Na+].[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[C:4]([CH2:3][NH:2][S:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:16])=[O:15])#[N:5]

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 3113398HCID 3113398, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 27.8 g (0.3 moles) aminoacetonitrile hydrochloride and 24.0 g (0.3 moles) 50% aqueous sodium hydroxide in 200 ml water, 17.7 g (0.1 mole) benzenesulfonyl chloride were dropped in over about 25 minutes. During the addition, the temperatures of the reaction mixture was kept under 20° C. using an ice bath. After the addition was complete, the ice bath was removed; stirring of the reaction mixture continued for about 30 minutes. The solids which formed were isolated by filtration and were washed with 200 ml water. The resulting beige solids were dissolved in 150 ml methylene chloride, dried over magnesium sulfate and stripped. The resulting white solids were washed with hexane, filtered and air-dried to give 13.9 g of the above-identified product, melting point 81°-83° C.

Workup

  1. additionDuring the addition
  2. customwas kept under 20° C.
  3. additionAfter the addition
  4. customthe ice bath was removed
  5. customThe solids which formed
  6. customwere isolated by filtration
  7. washwere washed with 200 ml water
  8. dissolutionThe resulting beige solids were dissolved in 150 ml methylene chloride
  9. dry with materialdried over magnesium sulfate
  10. washThe resulting white solids were washed with hexane
  11. filtrationfiltered
  12. customair-dried

Sources & evidence

ORD record
ord-be86876dcfe04f148af86ee3b3615f4a
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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