Dimethylformamide → 2-Methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazole-5-carbaldehyde

HRID 326085Notes

Reaction equation

HRID 326085 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[S:11][C:10]2=[N:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:14][N:9]2[N:8]=1.[OH-].[Na+].CN(C)[CH:25]=[O:26]>>[CH3:6][C:7]1[S:11][C:10]2=[N:12][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:14]([CH:25]=[O:26])[N:9]2[N:8]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 30000392-Methyl-6-phenylimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 127835242-Methyl-6-phenyl-imidazo[2,1-b]-1,3,4-thiadiazole-5-carbaldehyde

Conditions

Temperature
100 °C

Procedure

60 ml of phosphorus oxychloride were added dropwise to 180 ml of dimethylformamide, whilst cooling. A further 400 ml of dimethylformamide, and 130 g (0.6 mole) of 2-methyl-6-phenylimidazo[2,1-b]-1,3,4-thiadiazole were then added and the mixture was warmed to 100° C. for 2 hours. It was poured onto 3 kg of ice, 410 g of 40% strength sodium hydroxide solution were added and the mixture was heated rapidly to 90° C. After 5 minutes, it was cooled and the product was filtered off. Yield: 132 g (90% of theory) of melting point 152° to 153° C.

Workup

  1. temperaturewhilst cooling
  2. additionwere added
  3. temperaturethe mixture was heated rapidly to 90° C
  4. temperatureit was cooled
  5. filtrationthe product was filtered off

Sources & evidence

ORD record
ord-b0069be164944a62aa266a5457752301
Source dataset
uspto-grants-1984_04
Patent number
US04444770

Reaction notes

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