Ammonia → Naphthalenesulfonamide

HRID 1165521Notes

Reaction equation

HRID 1165521 reaction equation
[NH3:1].[C:2]1([S:12](Cl)(=[O:14])=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1>CCOCC>[C:2]1([S:12]([NH2:1])(=[O:14])=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 665601-Naphthalenesulfonyl chloride

Product 1

HCID 163571NaphthalenesulfonamideYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ammonia was passed (for 5 min) into a stirred solution of 1-naphthalenesulfonyl chloride (5.0 g, 22 mmol) and anhydrous Et2O (400 ml) at -78°. The resulting mixture was stirred at -78° for 1 hr, allowed to warm to room temperature, and stirred overnight. The Et2O was removed under vacuum to leave a white powder which was washed with water and dried under vacuum to give 3.2 g (70%) of the title compound as a white powder, m.p. 152°-153° C.

Workup

  1. custom(for 5 min)
  2. customat -78°
  3. stirringstirred overnight
  4. customThe Et2O was removed under vacuum
  5. customto leave a white powder which
  6. washwas washed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2462333a4fff4a13b66adbd440e7481b
Source dataset
uspto-grants-1990_03
Patent number
US04910190

Reaction notes

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