Sodium borohydride → HCID 58006844, compound

HRID 2264050Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:22])[C:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)=[N:11][S:10](=[O:21])(=[O:20])[NH:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:22])[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][S:10](=[O:21])(=[O:20])[NH:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3,4-bis-(4-chloro-phenyl)-3-methyl-2,3-dihydro-[1,2,5]thiadiazole 1,1-dioxide (5.38 g, 15.1 mmol) in 91 mL of in ethanol cooled to 0° C. was added sodium borohydride (0.30 g, 61 mmol) portionwise over 7 min. After stirring at 0° C. for another 45 min, the mixture was allowed to warm to room temperature and stirred for 3.5 h. The reaction was then cooled to 0° C. and quenched by dropwise addition of 1 M hydrochloric acid (38 mL). The reaction mixture was taken up in 500 mL of ethyl acetate then washed with water (300 mL) and brine (300 mL), dried over anhydrous sodium sulfate and concentrated. The crude residue was purified by flash column chromatography (silica gel, eluting with 3:1 heptane-ethyl acetate) to give rac-(3R*,4S*)-3,4-bis(4-chlorophenyl)-3-methyl-1,2,5-thiadiazolidine-1,1-dioxide (4.3 g).

Workup

temperatureto warm to room temperature
stirringstirred for 3.5 h
temperatureThe reaction was then cooled to 0° C.
customquenched by dropwise addition of 1 M hydrochloric acid (38 mL)
washthen washed with water (300 mL) and brine (300 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe crude residue was purified by flash column chromatography (silica gel, eluting with 3:1 heptane-ethyl acetate)

Sources & evidence

ORD record: ord-98711503ded549ffae8e01daf985c18d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851626B2

Reaction notes

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