Water → HCID 118353310, compound

HRID 921056Notes

Reaction equation

HRID 921056 reaction equation
N1C=CC=CC=1[C:7]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[NH2:9].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[N+:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30])([O-:22])=[O:21].O>C(Cl)Cl>[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:23]1([N+:20]([O-:22])=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]1[S:29]([NH:9][C:8]1[CH:7]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:30])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 4595162-(Pyridin-2-yl)aniline

Product 1

HCID 118353310HCID 118353310, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To 2-(2-pyridinyl)aniline (S1) (851 mg, 5.00 mmol, 1.00 equiv) in CH2Cl2 (10 mL) at 0 ° C. was added pyridine (1.60 mL, 20.0 mmol, 4.00 equiv) and 2-nitrobenzenesulfonyl chloride (2.20 g, 10.0 mmol, 2.00 equiv). The reaction mixture was warmed to 23 ° C. and stirred for 2.0 hr before the addition of water (10 mL). The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×8 mL). The combined organic phases were washed with brine (30 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 3:7 (v/v) to afford 1.33 g of the title compound as a pale-yellow solid (75%). Rf=0.12 (hexanes/EtOAc 7:3 (v/v)). Melting Point: 91-94 ° C. NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 ° C., δ): 8.73 (d, J=5.0 Hz, 1H), 7.94 (dd, J=7.5 Hz, 2.0 Hz, 1H), 7.82 (dd, J=8.0 Hz, 1.0 Hz, 1H), 7.74 (ddd, J=7.5 Hz, 7.5 Hz, 2.0 Hz, 1H), 7.63-7.52 (m, 5H), 7.38 (ddd, J=7.5 Hz, 7.5 Hz, 1.5 Hz, 1H), 7.27-7.24 (m, 1H), 7.18 (ddd, J=7.5 Hz, 7.5 Hz, 1.0 Hz, 1H). 13C NMR (125 MHz, CDCl3, 23 ° C., δ): 156.9, 156.2, 148.0, 137.9, 136.4, 133.6, 132.2, 131.0, 130.0, 129.0, 127.1, 125.0, 124.7, 122.4, 121.9, 121.9, 110.9. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [C17H13N3O4S+H], 356.06995. Found, 356.07008.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×8 mL)
  3. washThe combined organic phases were washed with brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 3:7 (v/v)

Sources & evidence

ORD record
ord-f565fe0bdf4d4447a11fcc0932c21cc9
Source dataset
uspto-grants-2016_03
Patent number
US09273083B2

Reaction notes

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