Chloroacetaldehyde → HCID 486298, compound

HRID 1073208Notes

Reaction equation

HRID 1073208 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[CH2:12][CH:13]=O>C(O)CCC>[N:1]1[CH:12]=[CH:13][N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[S:3][C:2]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 486298HCID 486298, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

In 250 ml of n-butanol were heated 10.0 g of 2-aminobenzothiazole and 30 ml of 40% chloroacetaldehyde at 90° C. for 27 hours. After the solvent was removed (evaporated to dryness), the residue was crystallized in isopropanol-acetone to give 6.2 g of imidazo[2,1-b]benzothiazole. Subsequently, 4.0 g of the crystals were added to a mixture of 50 ml of dry dimethylformamide and 3.5 ml of phosphorus oxychloride followed by heating at 60° C. for 3 hours and at 75° C. for 6 hours. After completion of the reaction, the reaction mixture was poured onto ice water. After neutralizing with potassium carbonate, the mixture was extracted with ethyl acetate. The ethyl acetate was removed to give 2.2 g of 3-formylimidazo[2,1-b]benzothiazole. The thus obtained formyl compound, 1.3 g, was added to 20 ml of ethanol and furthermore 0.1 g of sodium borohydride was added to the mixture while stirring under ice cooling. After stirring at the same temperature for 10 minutes, the solvent was removed. The residue was treated with water and filtered to give 1.2 g of the title compound.

Workup

  1. customAfter the solvent was removed
  2. custom(evaporated to dryness)
  3. customthe residue was crystallized in isopropanol-acetone

Sources & evidence

ORD record
ord-7ad41aeef0ca473698b3d41cf086a3d4
Source dataset
uspto-grants-1990_11
Patent number
US04968708

Reaction notes

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