Chloroacetaldehyde → 2-(Methylsulfanyl)imidazo[2,1-b][1,3,4]thiadiazole

HRID 1942317Notes

Reaction equation

HRID 1942317 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH3:8])=[N:5][N:6]=1.Cl[CH2:10][CH:11]=O.C(N(C(C)C)CC)(C)C.O>C(O)CCC>[CH3:8][S:7][C:4]1[S:3][C:2]2=[N:1][CH:10]=[CH:11][N:6]2[N:5]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 962WaterHCID 213905-(Methylsulfanyl)-1,3,4-thiadiazol-2-amineHCID 81531Diisopropylethylamine

Product 1

HCID 582857052-(Methylsulfanyl)imidazo[2,1-b][1,3,4]thiadiazoleYield 146.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Amino-5-methylthio-1,3,4-thiadiazole (10.00 g; 67.92 mmol; 1.00 eq.) was reluxed in 1-butanol (100.00 ml) until complete dissolution of starting material. Then, chloroacetaldehyde (21.91 ml; 169.81 mmol; 2.50 eq.) was slowly added and the reaction was refluxed for 2 h. Diisopropyethylamine (11.63 ml) was slowly added over 2 h using a syringe pump. After 18 h, the reaction was allowed to cool to room temperature. Then, water was added and the aqueous phase was extracted 4 times with EtOAc. The combined organics were washed with brine, dried over MgSO4 to give 17 g of a viscous brown oil. The crude was purified by flash chromatography (preabsorption using MeOH an silica) using 95/5 dichloromethane/methanol. The combined fractions gave 3.05 g of the desired product as a pale orange solid.

Workup

  1. temperaturethe reaction was refluxed for 2 h
  2. extractionthe aqueous phase was extracted 4 times with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9fe19f02da274372a7aeef9476037310
Source dataset
uspto-grants-2013_03
Patent number
US08389554B2

Reaction notes

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