Hydrogen Sulfide → HCID 22744791, compound

HRID 2223319Notes

Reaction equation

[SH2:1].C([S:4][C:5](=N)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[CH2:13][CH2:14][C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])C.Cl.CCOCC>O1CCCC1.O>[Br:21][C:19]1[CH:18]=[CH:17][C:16]([O:22][CH3:23])=[C:15]([CH2:14][CH2:13][C:7]2[C:8]([Cl:12])=[CH:9][CH:10]=[CH:11][C:6]=2[C:5]([SH:4])=[S:1])[CH:20]=1

Participants

Conditions

Temperature: 45 °C

Procedure

As shown in Scheme 9, hydrogen sulfide gas (2 mL) was condensed into a cooled (−78° C.) solution of 2.8 grams (6.8 mmol) of 2-[2-(5-Bromo-2-methoxy-phenyl)-ethyl]-3-chloro-thiobenzimidic acid ethyl ester and 13.6 mL (13.6 mmol) of 1.0 M HCl/ether in 100 mL of tetrahydrofuran. The reaction was heated to 45° C. and stirred overnight in a sealed tube. The reaction mixture was diluted with water and extracted with methylene chloride once, organic layer was washed with brine, dried (MgSO4), filtered and evaporated to give a crude orange oil. The oil was partially purified by chromatography through a short column of silica gel (eluting with 5:95 ethyl acetate/hexanes) which resulted in 1.8 g of an orange powder which was used directly.

Workup

customcondensed into
extractionextracted with methylene chloride once
washorganic layer was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customto give a crude orange oil
customThe oil was partially purified by chromatography through a short column of silica gel (eluting with 5:95 ethyl acetate/hexanes) which

Sources & evidence

ORD record: ord-7e7cb8d17a654d90bdcc2970412cc63e
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375125B2

Reaction notes

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