Hydrochloric Acid → HCID 57736333, compound

HRID 2261306Notes

Reaction equation

HRID 2261306 reaction equation
[C:1]([C:5]1[N:9]=[C:8]([C:10](OC)=[O:11])[S:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.Cl.C(=O)([O-])O.[Na+]>ClCCl.C1(C)C=CC=CC=1>[C:1]([C:5]1[N:9]=[C:8]([CH2:10][OH:11])[S:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21225700DiisobutylaluminumhydrideHCID 57736343HCID 57736343, compound

Product 1

HCID 57736333HCID 57736333, compoundYield 67.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

0.96 g of methyl 3-t-butyl-1,2,4-thiadiazole-5-carboxylate was dissolved in 48 ml of dichloromethane and then cooled to −78° C. under a nitrogen atmosphere. To the solution, 11 ml of a solution (1 mol/L) of diisobutylaluminum hydride in toluene was added and the mixture was stirred at 0° C. for 3 hours. After 10 ml of 1 mol/L hydrochloric acid was added, the reaction mixture was stirred for 10 minutes and 50 ml of aqueous saturated sodium hydrogen carbonate was then added. The reaction mixture was extracted with chloroform, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.56 g of (3-t-butyl-1,2,4-thiadiazol-5-yl)methanol.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. extractionThe reaction mixture was extracted with chloroform
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f101d6f5bc9647b595027b504bf9430f
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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