Methoxyacetic Acid → 5-(Methoxymethyl)-1,3,4-thiadiazol-2-amine

HRID 69557

Reaction equation

HRID 69557 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].[CH3:6][O:7][CH2:8][C:9](O)=O.P(Cl)(Cl)(Cl)=O.[Na]>O1CCOCC1.O>[CH3:6][O:7][CH2:8][C:9]1[S:4][C:3]([NH2:5])=[N:2][N:1]=1

Participants

7

Reactant 4

HCID 12251Methoxyacetic AcidHCID 24813Phosphorus oxychlorideHCID 2723789ThiosemicarbazideHCID 5360545Sodium

Product 1

HCID 6608445-(Methoxymethyl)-1,3,4-thiadiazol-2-amineYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of thiosemicarbazide a24 (40 g, 0.44 mol, 1 eq) in dioxane (400 ml) at room temperature is added methoxyacetic acid (39.56 g, 0.44 mol, 1 eq) in one portion, and the reaction mixture is heated at 80° C. then phosphorous oxychloride (67.54 g, 0.44 mol, 1 eq) is carefully added over 1.5 hours. After reaction completion (4 hours), water is added and the solution is neutralised to pH=6-7 with sodium hydroxyde pellets. After extraction EtOAc/iPrOH (9/1) and evaporation under vacuum, the residue is recrystallized from MeTHF/iPrOH to afford 51 g of pure 5-(methoxymethyl)-1,3,4-thiadiazol-2-amine a25.

Workup

  1. additionis added
  2. extractionAfter extraction EtOAc/iPrOH (9/1) and evaporation under vacuum
  3. customthe residue is recrystallized from MeTHF/iPrOH

Sources & evidence

ORD record
ord-06c0c059141a44578f5004c4a2aa0a42
Source dataset
uspto-grants-2014_09
Patent number
US08822508B2

Linked notes

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