Water → 2-[(Benzenesulfonyl)methyl]aniline

HRID 733042

Reaction equation

HRID 733042 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Sn].O>CO.Cl>[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3638902-Nitrobenzyl phenyl sulfoneHCID 5352426Tin atom

Product 1

HCID 108902352-[(Benzenesulfonyl)methyl]aniline

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A stirred mixture of 2-(phenylsulfonylmethyl)-1-nitrobenzene (5.55 g, 20.0 mmol) and granular tin (10.4 g, 88 mmol) in methanol and concentrated HCl (60 mL) is stirred under nitrogen at 45° C. for 5 h, cooled to ambient temperature over an 18 h period, poured onto NaHCO3 (80 g) with stirring, treated with water and extracted with ethyl acetate. The combined extracts are washed with brine (2×100 mL), dried over MgSO4, and concentrated in vacuo to afford the title product as an off-white solid, 4.41 g (89%) mp 175-176° C., identified by HNMR and mass spectral analyses.

Workup

  1. temperaturecooled to ambient temperature over an 18 h period
  2. additionpoured onto NaHCO3 (80 g)
  3. stirringwith stirring
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts are washed with brine (2×100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49c0602c74fa4cef90cf04d78cd001d5
Source dataset
uspto-grants-2009_09
Patent number
US07589108B2

Linked notes

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