Methanol → Methyl 4-({[2-(2,4-dichlorophenoxy)phenyl]amino}sulfonyl)phenylcarbamate

HRID 746742Notes

Reaction equation

HRID 746742 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)=C=O.CO.Cl.[Cl:17][C:18]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:19]=1[O:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23].[C:33]([O:36][CH2:37]C)(=[O:35])C>N1C=CC=CC=1>[Cl:17][C:18]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:19]=1[O:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][S:10]([C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:33](=[O:35])[O:36][CH3:37])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 81230p-Isocyanatobenzenesulphonyl chlorideHCID 2795482Benzenamine, 4-(2,4-dichlorophenoxy)-, hydrochloride

Product 1

HCID 58664942Methyl 4-({[2-(2,4-dichlorophenoxy)phenyl]amino}sulfonyl)phenylcarbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-isocyanatobenzenesulfonyl chloride (0.20 g, 0.92 mmol) in pyridine (0.92 mL) at 0° C. was added methanol (38 μL, 0.92 mmol). The ice bath was removed after 5 min, and the reaction mixture was slowly warmed to room temperature. After 1.5 hrs of stirring, 2-(2,4-dichloro-phenoxy)aniline hydrochloride (0.27 g, 0.92 mmol) was added. After 1.5 hrs of stirring, the reaction mixture was diluted with ethyl acetate and washed with 0.5 N HCl (×2), water (×2), half brine and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography eluted with 10-60% ethyl acetate in hexane to provide the title compound. MS (ES, M+H+): 467.0. 1H NMR (400 MHz, CD3OD) δ 7.62 (m, 3H), 7.48 (d, J=2.4 Hz, 1H), 7.43 (dd, J=9.2 Hz, 2H), 7.09 (m, 3H), 6.58 (m, 1H), 6.37 (d, J=8.8 Hz, 1H), 3.76 (s, 3H).

Workup

  1. customThe ice bath was removed after 5 min
  2. stirringAfter 1.5 hrs of stirring
  3. washwashed with 0.5 N HCl (×2), water (×2), half brine and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 10-60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fc55b920bc4e4fbebc6ba20bf5e0e60a
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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