Dimethylformamide → HCID 86744335, compound

HRID 1073220Notes

Reaction equation

HRID 1073220 reaction equation
Cl.[F:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]3[CH:12]=[C:11](C)[N:10]=[C:8]3[S:9][C:5]=2[CH:4]=1.P(Cl)(Cl)(Cl)=O.[C:21](=[O:24])([O-])[O-].[Na+].[Na+].[CH3:27]N(C)C=O>>[F:2][C:3]1[CH:15]=[CH:14][C:6]2[N:7]3[C:12]([CH:21]=[O:24])([CH3:27])[CH2:11][N:10]=[C:8]3[S:9][C:5]=2[CH:4]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 22158386HCID 22158386, compound

Product 1

HCID 86744335HCID 86744335, compound

Conditions

Temperature
60 °C

Procedure

The hydrochloride, 20.7 g, was added to 59.5 g of phosphorus oxychloride and 200 ml of dimethylformamide followed by heating at 60° C. for 3 hours. After completion of the reaction, the reaction solution was poured onto ice water containing sodium carbonate. The precipitated crystals were taken out by filtration and recrystallized from ethanol to give 8.77 g of 7-fluoro-3-formyl-3-methylimidazo[2,1-b]benzothiazole. Subsequently, the resulting formyl compound and 1.00 g of sodium borohydride were refluxed in ethanol for one hour. After completion of the reaction, ethanol was removed and the residue was recrystallized from methanol to give 2.74 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction solution was poured onto ice water
  3. filtrationThe precipitated crystals were taken out by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-13f13d78af314aaba39f3559a7fa7b7d
Source dataset
uspto-grants-1990_11
Patent number
US04968708

Reaction notes

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