1,3,4-Thiadiazol-2-amine → N-(2,4-dimethoxybenzyl)-1,3,4-thiadiazol-2-amine

HRID 46317

Reaction equation

HRID 46317 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[CH3:7][O:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.Cl[Ti](OC(C)C)(OC(C)C)OC(C)C>[CH3:7][O:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH2:11][NH:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 199091,3,4-Thiadiazol-2-amineHCID 691752,4-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58042278N-(2,4-dimethoxybenzyl)-1,3,4-thiadiazol-2-amineYield 45%

Reagents, catalysts & solvents 2

HCID 178460663HCID 178460663, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-1,3,4-thiadiazole (3.05 g, 0.0302 mol) and 2,4-dimethoxy-benzaldehyde (4.55 g, 0.0274 mol) in dichloromethane (125 mL) was added chlorotriisopropoxytitanium (16 mL, 0.067 mol) portionwise over 5 minutes. After stirring for 1 hour, sodium triacetoxyborohydride (11.72 g, 0.05530 mol) was added portion wise and stirred for 24 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution and adjusted to pH 9 with sodium hydroxide (6 N aqueous solution) and extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography eluting with methanol:dichloromethane (gradient 0:1 to 1:9, by volume) to afford the title compound as a white solid, 590 mg, 45% yield.

Workup

  1. stirringstirred for 24 hours
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography
  8. washeluting with methanol

Sources & evidence

ORD record
ord-015316899b3a4942a482a9e33c8ef297
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Linked notes

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