Pyridine → HCID 40532960, compound

HRID 1642121Notes

Reaction equation

HRID 1642121 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[Cl:25]>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([S:26]([NH:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])(=[O:27])=[O:28])[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8635Methyl Anthranilate

Product 1

HCID 40532960HCID 40532960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Methyl 2-aminobenzoate (10 g, 66.2 mmol) was dissolved in DCM (100 ml), and pyridine (8.1 ml, 99.2 mmol, 1.5 eq.) was added thereto. A solution of 3,4-dichlorobenzenesulfonyl chloride (24.4 g, 99.2 mmol, 1.5 eq.) in DCM (150 ml) was then added dropwise at 0° C., and the reaction mixture was stirred overnight at room temperature. TLC monitoring (silica gel, DCM) showed complete conversion. When the reaction was complete, the reaction solution was diluted with DCM (250 ml) and washed with 0.5 M KHSO4 (500 ml), saturated NaHCO3 (500 ml) and saturated NaCl solution (500 ml). The organic phase was dried over sodium sulfate and concentrated in vacuo. For purification, filtration over a thin layer of silica gel was carried out (gradient: heptane/DCM (3:1) to DCM).

Workup

  1. washwashed with 0.5 M KHSO4 (500 ml), saturated NaHCO3 (500 ml) and saturated NaCl solution (500 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. filtrationFor purification, filtration over a thin layer of silica gel

Sources & evidence

ORD record
ord-8abb147dd35e469a9906a598635bde4c
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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