Methanol → Sulindac Sulfide Methyl Ester

HRID 379619Notes

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:23].S(Cl)(Cl)=O.[CH3:29]O>>[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]([O:24][CH3:29])=[O:23]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 5352624Sulindac Sulfide

Product 1

HCID 16046334Sulindac Sulfide Methyl Ester

Procedure

To a suspension of (Z)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-ylacetic acid (51 g, 0.15 mol) in methanol (600 mL) at 0° C. there was slowly added thionyl chloride (26.8 g, 0.225 mol). The mixture was then stirred at room temperature for 2 hours and filtered to afford the title compound as a yellow solid, mp 73-75° C.

Workup

filtrationfiltered

Sources & evidence

ORD record: ord-bf08785bf95a42879efb64ff89146ef4
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300346B1

Reaction notes

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