Ammonium Hydroxide → HCID 54389224, compound

HRID 461471Notes

Reaction equation

HRID 461471 reaction equation
[C:1]1([CH:7]=[C:8]([S:10](Cl)(=[O:12])=[O:11])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+:15]>>[C:1]1([CH:7]=[C:8]([S:10]([NH2:15])(=[O:12])=[O:11])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 544016021-Phenylprop-1-ene-2-sulfonyl chloride

Product 1

HCID 54389224HCID 54389224, compound

Procedure

The 1-phenylpropene-2-sulfonyl chloride is added to 200 ml. of concentrated ammonium hydroxide. After one hour the crystalline precipitate which has formed is filtered off, and washed sequentially with water and hexane. The crude product so obtained is partitioned between 150 ml. of 1N sodium hydroxide and 50 ml. of ether, giving two clear phases. The ether phase is removed and washed with 50 ml. of water, and then the water wash is added to the original aqueous phase. This combined solution is acidified using concentrated hydrochloric acid, which causes the product to precipitate. It is filtered off, and after drying this affords 10.9g. of 1-phenylpropene-2-sulfonamide, m.p. 138°-139.5° C.

Workup

  1. customAfter one hour the crystalline precipitate which has formed
  2. filtrationis filtered off
  3. washwashed sequentially with water and hexane
  4. customThe crude product so obtained
  5. customis partitioned between 150 ml
  6. customof ether, giving two clear phases
  7. customThe ether phase is removed
  8. washwashed with 50 ml
  9. washof water, and then the water wash
  10. additionis added to the original aqueous phase
  11. customto precipitate
  12. filtrationIt is filtered off
  13. customafter drying this affords 10.9g

Sources & evidence

ORD record
ord-ecc4750f0b0547ca921e07003b25a328
Source dataset
uspto-grants-1977_12
Patent number
US04062960

Reaction notes

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