HCID 2757768, compound → HCID 15580444, compound

HRID 615172Notes

Reaction equation

HRID 615172 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[CH:16]=[O:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]3)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(Cl)(Cl)Cl.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[CH2:16][OH:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]3)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2757768HCID 2757768, compoundHCID 4311764Sodium borohydride

Product 1

HCID 15580444HCID 15580444, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 2 g of 2-(p-chlorophenyl)-3-formylimidazo[2,1-b]benzothiazole in 100 ml of chloroform and 200 ml of ethanol was added 1 g of sodium borohydride and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and 900 ml of chloroform was added to the residue. After removing the insoluble materials which formed, the residue was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue obtained was recrystallized from isopropyl alcohol to provide 1.2 g of 2-(p-chlorophenyl)-3-hydroxymethylimidazo[2,1-b]benzothiazole.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 900 ml of chloroform
  2. additionwas added to the residue
  3. customAfter removing the insoluble materials which
  4. customformed
  5. washthe residue was washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-d45ae3e89db64f57ad2cfc97fa737a24
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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