Pyridine → HCID 67130404, compound

HRID 2380969Notes

Reaction equation

HRID 2380969 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 67130533HCID 67130533, compound

Product 1

HCID 67130404HCID 67130404, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-(4-chloro-benzylamino)-benzoic acid tert-butyl ester (6 g, 6.3 mmol), phenylsulfonylchloride (2.9 ml, 21 mmol) and pyridine (1.86 mL, 23 mmol) in dichloromethane (25 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature, diluted with dichloromethane (25 ml) and washed with water (2×25 ml). The organics were collected, dried over magnesium sulfate and concentrated in vacuo to afford a yellow oil which was purified by flash chromatography (hexanes/ethyl acetate 9:1) to afford the title compound as a white solid (2.2 g, 76% yield). HPLC retention time 8.54 min.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. washwashed with water (2×25 ml)
  4. customThe organics were collected
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil which
  8. customwas purified by flash chromatography (hexanes/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-8fca8926549c4d4e888f1593296d4d68
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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