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

HRID 1396038Notes

Reaction equation

HRID 1396038 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, 1H).

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-3f6965ee88f547218d2d8b74715ca980
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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