Pyridine → HCID 22663775, compound

HRID 392470Notes

Reaction equation

HRID 392470 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].N1C=CC=CC=1.[N+:16]([C:19]1[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[N:4]([CH3:5])[S:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([N+:16]([O-:18])=[O:17])[CH:20]=1)(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 1049PyridineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 136736Benzenamine, 2-chloro-N-methyl-

Product 1

HCID 22663775HCID 22663775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-N-methylaniline (4.96 mmol, 1.1 eq., 702 mg) and pyridine (5.86 mmol, 464 mg) in 20 mL of methylene chloride was added 3-nitrobenzenesulfonyl chloride (4.51 mmol, 1.0 g) in one portion. The reaction mixture was stirred 16 hr and diluted with methylene chloride and water. The aqueous layer was separated and extracted once with methylene chloride. The combined organic layers were extracted once with a saturated solution of aqueous sodium carbonate, once with water, and then dried over sodium sulfate. The crude product was purified using flash chromatography (10-60% ethyl acetate/hexane) to give N-(2-chlorophenyl)-N-methyl-(3-nitrophenyl)sulfonamide which solidifies on standing. 1H NMR (300 MHz) 3.29 (s, 3H), 7.25-7.45 (m, 4H), 7.71 (t, J=7.82 Hz, 1H), 8.06 (d, J=7.82 Hz, 1H), 8.40-8.50 (m, 1H), 8.60-8.65 (m, 1H). MS (ESI): m/e 327.13, 329.13 (M+1).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted once with methylene chloride
  3. extractionThe combined organic layers were extracted once with a saturated solution of aqueous sodium carbonate, once with water
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-03f8c6564c104594818fc26b985f44f6
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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