Ethyl 2-(4-methylphenylsulfonamido)acetate → Ethyl 2-(((2-Ethoxy-2-oxoethyl)((4-methylphenyl)sulfonyl)amino)methyl)-5-iodonicotinate

HRID 1581562Notes

Reaction equation

HRID 1581562 reaction equation
Br[CH2:2][C:3]1[N:13]=[CH:12][C:11]([I:14])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])(=[O:24])=[O:23])=[CH:18][CH:17]=1.[O-]CC.[Na+]>C(O)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][N:25]([CH2:2][C:3]1[N:13]=[CH:12][C:11]([I:14])=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])[S:22]([C:19]1[CH:18]=[CH:17][C:16]([CH3:15])=[CH:21][CH:20]=1)(=[O:23])=[O:24])[CH3:31]

Participants

5

Reactant 3

HCID 230685Ethyl 2-(4-methylphenylsulfonamido)acetateHCID 2723922Sodium ethoxideHCID 22722039Ethyl 2-(Bromomethyl)-5-iodonicotinate

Product 1

HCID 22722035Ethyl 2-(((2-Ethoxy-2-oxoethyl)((4-methylphenyl)sulfonyl)amino)methyl)-5-iodonicotinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl 2-(bromomethyl)-5-iodonicotinate (Preparation 10, 9.25 g) and ethyl (((4-methylphenyl)sulfonyl)amino)acetate (7.0 g) are dissolved in anhydrous ethanol (50 mL) and a solution of sodium ethoxide (3.4 g) in ethanol (45 mL) is added over 15 min. The mixture is stirred overnight and then poured into ice water. The mixture is extracted with ethyl acetate (3×100 mL) and the organic layer is concentrated.

Workup

  1. extractionThe mixture is extracted with ethyl acetate (3×100 mL)
  2. concentrationthe organic layer is concentrated

Sources & evidence

ORD record
ord-cc8685b670424486925ff0b9928943e4
Source dataset
uspto-grants-2004_05
Patent number
US06730682B2

Reaction notes

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