1,3,4-Thiadiazole, 2-amino-5-methyl- → HCID 54253025, compound

HRID 612397Notes

Reaction equation

HRID 612397 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[C:8](N1C=CN=C1)(N1C=CN=C1)=[O:9].C(O[C:23](=[O:34])[C:24]([NH2:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:25][CH3:26])C>O1CCCC1>[CH2:25]([C:24]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:33][C:8](=[O:9])[N:1]([C:2]2[S:3][C:4]([CH3:7])=[N:5][N:6]=2)[C:23]1=[O:34])[CH3:26]

Participants

5

Reactant 3

HCID 669491,3,4-Thiadiazole, 2-amino-5-methyl-HCID 682631,1'-CarbonyldiimidazoleHCID 10488547ethyl 2-amino-2-phenylbutanoate

Product 1

HCID 54253025HCID 54253025, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

2.30 g of 2-amino-5-methyl-1,3,4-thiadiazole were dissolved at room temperature in 40 ml of dry tetrahydrofuran in a nitrogen atmosphere and with exclusion of moisture. 3.24 g of 1,1'-carbonyldiimidazole were then added. The mixture was stirred for 30 minutes at 50° C. 4.15 g of 2-amino-2-phenylbutyric acid ethyl ester (product from Example 3, stage 1) in 10 ml of dry tetrahydrofuran were added dropwise to the resultant suspension and stirred for 20 hours at 50° C. Once the solvent had been removed by distillation, the residue was recrystallised from ethanol. 3.94 g of 5-ethyl-3-(5-methyl[l.3.4]thiadiazol-2-yl)-5-phenyl-2,4-imidazolidinedione (58% of th.) were obtained in the form of white crystals (mp 223-225° C.).

Workup

  1. stirringstirred for 20 hours at 50° C
  2. customOnce the solvent had been removed by distillation
  3. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-3883975c18154d39a0925d7907c6033c
Source dataset
uspto-grants-1999_12
Patent number
US06004963

Reaction notes

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