Oxalyl chloride → (Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indenylacetyl chloride

HRID 377742Notes

Reaction equation

HRID 377742 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22]([OH:24])=O.C(Cl)(=O)C([Cl:28])=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][C:22]([Cl:28])=[O:24]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 5352624Sulindac Sulfide

Product 1

HCID 88255253(Z)-5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)-3-indenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-5-fluoro-2-methyl-1-(4-methythiobenzylidene)-3-indenylacetic acid (70 mmol) in THF (500 ml) is allowed to react with oxalylchloride (2 M in CH2Cl2 ; 35 ml) under reflux conditions (24 hours). The solvent is evaporated to yield the title compound, which is used as such in the next step.

Workup

  1. customThe solvent is evaporated

Sources & evidence

ORD record
ord-7e99e7b5e37b4901afa446cb2498d348
Source dataset
uspto-grants-2000_02
Patent number
US06028116

Reaction notes

Loading…