Benzenesulfonyl chloride → HCID 69517740, compound

HRID 1180012Notes

Reaction equation

HRID 1180012 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19](=[O:28])[N:20]([CH3:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][CH:17]=1.C(N(CC)CC)C>ClCCl>[C:1]1([S:7]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][C:19](=[O:28])[N:20]([CH3:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:16][CH:17]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 69465626HCID 69465626, compound

Product 1

HCID 69517740HCID 69517740, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzenesulphonyl chloride (0.18 g, 1.00 mmol), dissolved in a small amount of dichloromethane, was added dropwise to a stirred solution of methyl-phenyl-carbamic acid 5-amino-pyridin-2-yl ester (0.24 g, 1.00 mmol) and triethylamine (0.10 g, 1.00 mmol) in dichloromethane (10 mL). After stirring for 4 hours the solution was extracted with water and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 40:60 followed by 50:50) yielding the title compound (108 mg, 23% yield) as a white solid.

Workup

  1. extractionwas extracted with water
  2. customevaporated in vacuo
  3. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 40:60 followed by 50:50)

Sources & evidence

ORD record
ord-7b2954ff7e694f85a717795e08adfd98
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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