Pyridine → 3-(3-Chloro-propane-1-sulfonylamino)-5-methylsulfanyl-benzoic acid methyl ester

HRID 852556Notes

Reaction equation

HRID 852556 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH2:13])[CH:6]=1.N1C=CC=CC=1.[Cl:21][CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[C:7]([NH:13][S:25]([CH2:24][CH2:23][CH2:22][Cl:21])(=[O:27])=[O:26])[CH:6]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 693575963-Amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride

Product 1

HCID 693568243-(3-Chloro-propane-1-sulfonylamino)-5-methylsulfanyl-benzoic acid methyl esterYield 104.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-5-methylsulfanyl-benzoic acid methyl ester hydrochloride (D62) (130 mg, 0.556 mmol, 1 equiv) in CH2Cl2 (2 ml) was added pyridine (142 ml, 1.75 mmol, 3 equiv), DMAP (6.8 mg, 0.056 mmol, 0.1 equiv) and then 3-chloropropane sulfonyl chloride (71 μl, 0.584 mmol, 1.05 equiv) dropwise over 2 min. The resulting mixture was stirred at room temperature for 2 h, diluted with AcOEt, washed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo to give 3-(3-chloropropane-1-sulfonylamino)-5-methylsulfanyl-benzoic acid methyl ester (D66) (196 mg, 104%) as light brown crystals. [M−H]−=336.0 RT=3.20 min

Workup

  1. washwashed sequentially with 2N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a58c02aae1ba4eb0b5879e79f346fa6e
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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