Lithium borohydride → HCID 90460960, compound

HRID 2202114Notes

Reaction equation

HRID 2202114 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:14](OC)=[O:15])=[N:11][S:12][N:13]=2)=[CH:5][CH:4]=1)#[N:2].[Li+].[BH4-]>O1CCCC1>[OH:15][CH2:14][C:10]1[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[N:13][S:12][N:11]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 90462801HCID 90462801, compound

Product 1

HCID 90460960HCID 90460960, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(4-cyanophenyl)-1,2,5-thiadiazole-3-carboxylate (260 mg, 1.06 mmol, 1.00 equiv) in anhydrous tetrahydrofuran (20 mL) maintained under nitrogen at −5° C. was added LiBH4 (117 mg, 5.32 mmol, 5.02 equiv) portion-wise. The reaction was stirred at room temperature for 1.5 h and then quenched with 5 mL of saturated NH4Cl solution. The mixture was extracted with 3×20 mL of ethyl acetate. The combined organic layers were washed with 3×100 mL of brine, dried over anhydrous sodium sulfate and concentrated to afford 230 mg (100%) of 4-(4-(hydroxymethyl)-1,2,5-thiadiazol-3-yl)benzonitrile as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6): δ 8.12 (d, J=8.4 Hz, 2H), 8.03 (d, J=8.4 Hz, 2H), 4.81 (s, 2H) ppm.

Workup

  1. customquenched with 5 mL of saturated NH4Cl solution
  2. extractionThe mixture was extracted with 3×20 mL of ethyl acetate
  3. washThe combined organic layers were washed with 3×100 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ed1b40ed38a146d08c4fa1b9d3bc82f6
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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