Magnesium chloride hexahydrate → HCID 86730375, compound

HRID 1500385Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:8]#[N:9])([CH3:3])[CH3:2].O.[SH2:18].[Na].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(OCC)(=O)C.CCCCCC>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:8](=[S:18])[NH2:9])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 27.5 °C

Procedure

3-Isopropoxy-5-(trifluoromethyl)benzonitrile (1000 g, 4.3 moles) was dissolved in DMF (4000 mL) and sodium hydrogensulfide hydrate (636 g; 8.6 moles) was added followed by magnesium chloride hexahydrate (960.2 g, 4.7 moles). The reaction mixture was stirred for 1 hr at 25 to 30° C. Reaction completion was monitored by TLC using ethyl acetate:hexane (2:8) as the mobile phase. The reaction mixture was quenched in an ice-water slurry (250 mL) and the pH was adjusted to 5 by addition of 10% aqueous HCl. The reaction mixture was extracted with MTBE and was washed with 20% brine solution. The organic layer was concentrated under vacuum to give 1136 g (4.3 moles; 100%) of the title compound, which was taken as such to next step. HPLC purity—97.37% a/a.

Workup

customReaction completion
customThe reaction mixture was quenched in an ice-water slurry (250 mL)
additionthe pH was adjusted to 5 by addition of 10% aqueous HCl
extractionThe reaction mixture was extracted with MTBE
washwas washed with 20% brine solution
concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record: ord-ab95da8b4ebb447e8bbdf2a9bcaa6d1b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206158B2

Reaction notes

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