Dimethylformamide → 6-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde

HRID 1851716Notes

Reaction equation

HRID 1851716 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[N:8]=[C:9]2[N:13]([CH:14]=1)[N:12]=[C:11]([CH2:15][O:16][CH3:17])[S:10]2.CN(C)[CH:20]=[O:21]>>[Cl:6][C:7]1[N:8]=[C:9]2[N:13]([C:14]=1[CH:20]=[O:21])[N:12]=[C:11]([CH2:15][O:16][CH3:17])[S:10]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 671165026-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 835264526-Chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehydeYield 79%

Conditions

Temperature
0 °C

Procedure

Phosphorus oxychloride (2.75 ml, 3 eq) is added very slowly to dimethyl formamide (5 ml) cooled at 0° C. The temperature rises to 50° C. The reaction mixture is heated at 60° C., then 6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazole a15 (2 g, 9.82 mmol, 1 eq) is added portionwise for 2.5 h. The reaction mixture is poured on an ice/water mixture. The precipitate is filtered and washed with water. The residue is dried overnight at 40° C. under reduced pressure to afford 1.8 g of 6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde a16 as a solid.

Workup

  1. customrises to 50° C
  2. temperatureThe reaction mixture is heated at 60° C.
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customThe residue is dried overnight at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-436e738a46af43a782aa42d4e9fc93ef
Source dataset
uspto-grants-2015_02
Patent number
US08957218B2

Reaction notes

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