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

HRID 2040147Notes

Reaction equation

HRID 2040147 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-e7f4e0b8b0e54d8a873a8edc8feeb4bf
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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