Stannous chloride dihydrate → HCID 22663625, compound

HRID 392471Notes

Reaction equation

HRID 392471 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:21])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)(=[O:11])=[O:10].O.O.[Sn](Cl)Cl>CO.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH3:21])[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22663775HCID 22663775, compound

Product 1

HCID 22663625HCID 22663625, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent2×

Procedure

A solution of N-(2-chlorophenyl)-N-methyl-(3-nitrophenyl)sulfonamide (2.6 mmol, 848 mg) and tin (II) chloride dihydrate (10.4 mmol, 2.35 g) were heated for 4 hr at reflux in 15 mL of methanol. The reaction mixture was cooled to room temperature and diluted with 20 mL of ethyl acetate and 10 mL of a saturated solution of aqueous sodium carbonate. Heavy gas evolution was observed upon addition of aqueous sodium carbonate to the reaction mixture. The reaction mixture was stirred 1 hr and then filtered through a plug of Celite®. The layers were separated and the organic layer was extracted once with a saturated solution of aqueous sodium carbonate, once with brine, and then dried with sodium sulfate. The crude product was purified using flash chromatography (0-5% ethyl acetate/methylene chloride) to give N-(2-chlorophenyl)-N-methyl-(3-aminophenyl)sulfonamide as an off white foam. 1H NMR (300 MHz) 3.13 (s, 3H), 3.80 (br s, 2H), 6.80-6.87 (m, 1H), 7.02-7.25 (m, 6H), 7.30-7.38 (m, 1H). MS (ESI): m/e 297.2, 299.2 (M+1).

Workup

  1. filtrationfiltered through a plug of Celite®
  2. customThe layers were separated
  3. extractionthe organic layer was extracted once with a saturated solution of aqueous sodium carbonate, once with brine
  4. dry with materialdried with sodium sulfate
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-4de48d3fbb1e4a95ac3a995885cdff6c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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