BENZENAMINE, 4-[(4-FLUOROPHENYL)SULFONYL]- → HCID 12011164, compound

HRID 897154Notes

Reaction equation

HRID 897154 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:18]([O-])=O.[Na+]>Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 572814BENZENAMINE, 4-[(4-FLUOROPHENYL)SULFONYL]-HCID 23668193Sodium Nitrite

Product 1

HCID 12011164HCID 12011164, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 4-[(4-fluorophenyl)sulfonyl]phenylamine (IV, Step II, 3.10 g, 12.3 mmol) in concentrated hydrochloric acid (30 mL) at 0° is treated with sodium nitrite (934 mg, 13.5 mmol) in H2O (15 mL). After 30 min, the mixture is treated with stannous chloride (5.57 g, 24.7 mmol) in concentrated hydrochloric acid (15 mL). The mixture is stirred at 0° for 1 hr, and then at 20-25° for 1 hr. The precipitate is collected and slurried in H2O. The mixture is made basic (sodium hydroxide, 50%) and the solid isolated. The material is partitioned between methylene chloride and saline. The organic layer is dried, filtered, and concentrated under reduced pressure to give the title compound, NMR (300 MHz, CDCl3) 7.85-7.95, 7.74, 7.13, 6.85, 5.64 and 3.65 δ.

Workup

  1. waitat 20-25° for 1 hr
  2. customThe precipitate is collected
  3. customthe solid isolated
  4. customThe material is partitioned between methylene chloride and saline
  5. customThe organic layer is dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6de9ae2241c2499a9e6a77edb7002214
Source dataset
uspto-grants-2005_07
Patent number
US06921823B2

Reaction notes

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