Acetic Acid → HCID 72347159, compound

HRID 1363317Notes

Reaction equation

C(O)(=O)C.[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:12]=[C:13]([CH:16]=O)[S:14][CH:15]=2)=[CH:8][CH:7]=1.[S:20]1[CH2:26][C:24](=[O:25])[NH:23][C:21]1=[S:22].C([O-])(=O)C.[Na+]>O>[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:26]3[S:20][C:21](=[S:22])[NH:23][C:24]3=[O:25])[S:14][CH:15]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 20-mL scintillation vial fitted with a magnetic stir bar was added 3 mL of glacial acetic acid (AcOH). The vial was capped tightly and heated to 80° C. To the hot AcOH was added 4-(4-chlorobenzyl)thiophene-2-carbaldehyde (example 1.1.a); 0.37 g, 1.56 mmol, 1 equiv) and rhodanine (0.23 g, 1.7 mmol, 1.1 equiv) with stirring until a solution was formed. To the mixture was then added anhydrous sodium acetate (0.45 g, 5.5 mmol, 3.5 equiv), and the vial was capped tightly and heated to 110° C. for approx. 1 h. The reaction vial was cooled to rt and the contents were poured into water. The resulting precipitate was filtered, washed with water and a cold mixture of 1:1 water/ethanol. The solid was dried thoroughly in vacuo at 40° C. to give 5-((4-(4-chlorobenzyl)thiophen-2-yl)methylene)-2-thioxothiazolidin-4-one (451 mg, 81%). 1H NMR (400 MHz, (CD3)2SO) δ (ppm): 7.70 (s, 1H), 7.67 (s, 1H), 7.46 (s, 1H), 7.34-7.38 (m, 2H), 7.25-7.29 (m, 2H), 3.96 (s, 2H).

Workup

customTo a 20-mL scintillation vial fitted with a magnetic stir bar
customThe vial was capped tightly
customwas formed
temperatureheated to 110° C. for approx. 1 h
customThe reaction
temperaturevial was cooled to rt
filtrationThe resulting precipitate was filtered
washwashed with water
additiona cold mixture of 1:1 water/ethanol
customThe solid was dried thoroughly in vacuo at 40° C.

Sources & evidence

ORD record: ord-6cc4afb5206048488d77a228d37bcab1
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07884124B2

Reaction notes

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