Ammonium Hydroxide → 3-Fluoro-4-nitrobenzene-1-sulfonamide

HRID 2273951Notes

Reaction equation

HRID 2273951 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:11](Cl)(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[OH-].[NH4+:16]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([S:11]([NH2:16])(=[O:13])=[O:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 155695553-Fluoro-4-nitrobenzenesulfonyl chloride

Product 1

HCID 581586953-Fluoro-4-nitrobenzene-1-sulfonamideYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5.00 g 3-fluoro-4-nitrobenzenesulfonyl chloride in 20 mL acetonitrile cooled in an ice bath was added dropwise 4.40 mL of a 30% ammonium hydroxide solution. After removal of the ice bath, stirring was continued for 30 min. at room temperature. Water was added and the mixture was extracted with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness to give 4.65 g (99%) of a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.51 (s, 2H), 7.89 (d, J=9.33 Hz, 1H), 7.92 (dd, J=10.23, 1.81 Hz, 1H), 8.14-8.21 (m, 1 H).

Workup

  1. customAfter removal of the ice bath
  2. additionWater was added
  3. extractionthe mixture was extracted with DCM
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7d17c07b15ba454989aa2cb3c6f663aa
Source dataset
uspto-grants-2015_09
Patent number
US09126942B2

Reaction notes

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