Ammonia → 3-Cyano-4-fluorobenzene-1-sulfonamide

HRID 2167971Notes

Reaction equation

HRID 2167971 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10](Cl)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[NH3:14]>O1CCOCC1.CO>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH2:14])(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 27789083-Cyano-4-fluorobenzenesulfonyl chloride

Product 1

HCID 251398973-Cyano-4-fluorobenzene-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Cyano-4-fluorobenzene-1-sulfonyl chloride (1.1 g) in 1,4-dioxane (10 mL) at 0° C. was treated dropwise with a 7 M ammonia solution in methanol (3.57 mL) and stirred for 30 minutes. A small amount of solid was removed by filtration and discarded. The filtrate was concentrated, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, concentrated and triturated with diethyl ether to give the product.

Workup

  1. customA small amount of solid was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customtriturated with diethyl ether
  9. customto give the product

Sources & evidence

ORD record
ord-c3cf9d08b5b64bfab0ec9caa4c99e9c4
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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