3-Chloro-2-methylbenzenesulfonyl chloride → vinyl sulfonate 3-chloro-2-methyl-benzenesulfonic acid 1-[1-[6-(3-chloro-2-methyl-benzenesulfonylamino)-pyridin-2-yl]-meth-(Z)-ylidene]-butyl ester

HRID 1454812Notes

Reaction equation

HRID 1454812 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:16]([CH3:25])=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:14][C:15]1[C:16]([CH3:25])=[C:17]([S:21]([NH:1][C:2]2[N:7]=[C:6](/[CH:8]=[C:9](\[O:13][S:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[C:16]=3[CH3:25])(=[O:22])=[O:23])/[CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][CH:3]=2)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.[CH:17]([S:21]([OH:23])(=[O:13])=[O:22])=[CH2:18]

Participants

5

Reactant 2

HCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 688418781-(6-Amino-pyridin-2-yl)-pentan-2-one

Product 1

HCID 131727252vinyl sulfonate 3-chloro-2-methyl-benzenesulfonic acid 1-[1-[6-(3-chloro-2-methyl-benzenesulfonylamino)-pyridin-2-yl]-meth-(Z)-ylidene]-butyl esterYield 11.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(6-Amino-pyridin-2-yl)-pentan-2-one (0.15 g) in CH2Cl2 (5 mL) was treated at RT with 4-dimethylaminopyridine (0.103 g), 3-chloro-2-methyl-benzenesulfonyl chloride (0.208 g) and stirred at RT for 16 h. The mixture was partitioned between cold diluted aqueous HCl and AcOEt, the layers were separated, and the organic layer twice extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and evaporated. From the residue was isolated by flash chromatography (heptane/EtOAc 1:1) the vinyl sulfonate 3-chloro-2-methyl-benzenesulfonic acid 1-[1-[6-(3-chloro-2-methyl-benzenesulfonylamino)-pyridin-2-yl]-meth-(Z)-ylidene]-butyl ester (23 mg) as an amorphous off-white solid (27 mg). MS (ESI−): 552.8 ([M−H]−).

Workup

  1. customThe mixture was partitioned between cold diluted aqueous HCl and AcOEt
  2. customthe layers were separated
  3. extractionthe organic layer twice extracted with AcOEt
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7871a6574ef544439d0bc30e7495d833
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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