Water → 2-Chloro-5-methoxybenzene-1-sulfonamide

HRID 1474162Notes

Reaction equation

HRID 1474162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[OH-].[NH4+:15].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[S:10]([NH2:15])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 220335362-Chloro-5-methoxybenzene-1-sulfonyl chloride2×

Product 1

HCID 3140422-Chloro-5-methoxybenzene-1-sulfonamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-methoxybenzenesulfonyl chloride (2.5 g, 10.4 mmol) (i.e. the product of Step A) in tetrahydrofuran (30 mL) was added 30% ammonium hydroxide (3.0 mL, 25.7 mmol) dropwise. The reaction mixture was stirred for 15 minutes, during which time a suspension formed. To this mixture water (10 mL) was added, and the tetrahydrofuran was evaporated under reduced pressure to leave an aqueous suspension of a tan solid. The solid was isolated by filtration and washed with water to afford 2.2 g of the title compound. 1H NMR (CDCl3) δ 7.63 (d, 1H), 7.43 (d, 1H), 7.03 (d, 1H), 5.13 (br s, 2H), 3.85 (s, 3H).

Workup

  1. customformed
  2. customthe tetrahydrofuran was evaporated under reduced pressure
  3. customto leave
  4. additionan aqueous suspension of a tan solid
  5. customThe solid was isolated by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-0edc469e0c2c4a7693bfb0ba73099da6
Source dataset
uspto-grants-2015_04
Patent number
US09018228B2

Reaction notes

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