Triethylamine → 8-Chloro-6-(1-ethylpyrazol-5-yl)oxycarbonyl-5-methylthiochroman-4-one

HRID 1275443Notes

Reaction equation

[C:1]([C:4]1[C:5]([CH3:16])=[C:6]2[C:11](=[C:12]([Cl:14])[CH:13]=1)[S:10][CH2:9][CH2:8][C:7]2=[O:15])([OH:3])=[O:2].S(Cl)(Cl)=O.[CH2:21]([N:23]1[C:27](O)=[CH:26][CH:25]=[N:24]1)[CH3:22].C(N(CC)CC)C>C(Cl)Cl>[Cl:14][C:12]1[CH:13]=[C:4]([C:1]([O:3][C:27]2[N:23]([CH2:21][CH3:22])[N:24]=[CH:25][CH:26]=2)=[O:2])[C:5]([CH3:16])=[C:6]2[C:11]=1[S:10][CH2:9][CH2:8][C:7]2=[O:15]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture containing 2.0 g (7.8 mmol) of 6-carboxy-8-chloro-5-methylthiochroman-4-one and 2.8 g (3.0 eq., 24 mmol) of thionyl chloride was stirred under heat at 40° C. for 2 hours. After the completion of the reaction, excess thionyl chloride was removed under reduced pressure. Then, the resultant acid chloride was dissolved in 10 ml of methylene chloride, and 0.96 g (1.1 eq., 8.6 mmol) of 1-ethyl-5-hydroxypyrazole and 0.95 ml (9.41 mmol) of triethylamine were added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with methylene chloride, washed with diluted hydrochloric acid and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 2.29 g (yield 84%) of 8-chloro-6-(1-ethylpyrazol-5-yl)oxycarbonyl-5-methylthiochroman-4-one.

Workup

customwas removed under reduced pressure
dissolutionThen, the resultant acid chloride was dissolved in 10 ml of methylene chloride
stirringThe mixture was stirred at room temperature for 3 hours
washwashed with diluted hydrochloric acid and with a saturated sodium chloride aqueous solution
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-9215bac86bf34079ba382215c1c3bc05
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159904

Reaction notes

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