Benzenesulfonyl chloride → HCID 21706478, compound

HRID 1005400Notes

Reaction equation

HRID 1005400 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[C:10]([N+:17]([O-:19])=[O:18])[C:9]2=[O:20])=[CH:5][CH:4]=1.C1(S(Cl)(=O)=O)C=CC=CC=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH:13]=[CH:12][C:11]([CH:14]=[CH2:15])=[C:10]([N+:17]([O-:19])=[O:18])[C:9]2=[O:20])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 541704571-(4-Methoxybenzyl)-4-hydroxyethyl-3-nitro-2-pyridone

Product 1

HCID 21706478HCID 21706478, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-methoxybenzyl)-4-hydroxyethyl-3-nitro-2-pyridone (0.35 g, 1.2 mmol) in pyridine (4 mL) was added benzenesulfonyl chloride (0.2 mL). After 4 days, the mixture was diluted with ethyl acetate, and washed with dilute hydrochloric acid. The aqueous phase was basified to pH 13 with aqueous KOH, and after 30 minutes was extracted with ethyl acetate. The organic phase was dried, filtered and evaporated to give 1-(4-methoxybenzyl)-4-vinyl-3-nitro-2-pyridone (0.29 g, 1.0 mmol, 83%).

Workup

  1. washwashed with dilute hydrochloric acid
  2. extractionafter 30 minutes was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ee19d427c10743afa71c4066ff9f17d8
Source dataset
uspto-grants-2000_04
Patent number
US06054470

Reaction notes

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