Sodium Hydroxide → 3-(4-Phenylthiophen-2-yl)-2-thioxopropanoic acid

HRID 1397214Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[C:13]3[S:17]C(=S)N[C:14]3=[O:19])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:20].[Na+]>O>[C:1]1([C:7]2[CH:8]=[C:9]([CH2:12][C:13](=[S:17])[C:14]([OH:19])=[O:20])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A suspension of product 5-((4-phenylthiophen-2-yl)methylene)-2-thioxothiazolidin-4-one (1.4 g, 4.6 mmol) in 12 mL of 10% aqueous NaOH was heated to 95° C. for 1 h. The solution was cooled to room temperature and diluted with water. The aqueous phase was washed with EtOAc, and acidified with 10% HCl. The precipitate that was formed was filtered, washed with water and dried under reduced pressure to get the product 3-(4-phenylthiophen-2-yl)-2-thioxopropanoic acid (0.9 g, yield 74%). MS (ESI) m/z: Calculated for C13H10O2S2: 262.01. found: 261.0 (M−H)−. The crude product was carried through without further purification

Workup

temperatureThe solution was cooled to room temperature
washThe aqueous phase was washed with EtOAc
customThe precipitate that was formed
filtrationwas filtered
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-eb4daf333b924b258f8aa2a2a6fee004
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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