Ammonium Chloride → [6-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanol

HRID 1851717Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[CH:10]=[O:11])[N:7]=[C:6]([CH2:12][O:13][CH3:14])[S:5]2.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]2[N:8]([C:9]=1[CH2:10][OH:11])[N:7]=[C:6]([CH2:12][O:13][CH3:14])[S:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde a16 (2.97 g, 12.94 mmol, 1 eq) is dissolved in ethanol (80 ml), cooled at 0° C. and sodium borohydride (578 mg, 15.53 mmol, 1.2 eq) is added portionwise at 0° C. The reaction mixture is stirred overnight at room temperature, then cooled at 0° C. and a saturated NH4Cl aqueous solution (100 ml) is added. The organic solvent is evaporated under reduced pressure and the precipitate is filtered, dried under vacuum at 20° C. to afford 1.99 g of [6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methanol a17.

Workup

temperaturecooled at 0° C.
customThe organic solvent is evaporated under reduced pressure
filtrationthe precipitate is filtered
customdried under vacuum at 20° C.

Sources & evidence

ORD record: ord-92358bede8c44690a9b59d95495a4b41
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957218B2

Reaction notes

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