Acetic Acid → HCID 21278897, compound

HRID 2291587Notes

Reaction equation

HRID 2291587 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17](N)[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.C=O.[C:24]([BH3-])#[N:25].[Na+].[C:28](O)(=O)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([N:25]([CH3:24])[CH3:28])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 212788513-[2-(4-Aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2(3H)-one

Product 1

HCID 21278897HCID 21278897, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-chloro-3-[(4-amino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (1.64 g) in acetonitrile (50 ml) were added 37% formaldehyde solution (4 ml) and sodium cyanoborohydride (1 g) and the mixture was stirred for 25 minutes at room temperature and further for 1 hour neutralizing with acetic acid and concentrated. To a residue was added saturated sodium carbonate solution and extracted with chloroform. After drying over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure. The residue was subjected to a column chromatography on silica gel (42 g) and eluted with a mixture of chloroform-methanol (20:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was washed with ether and then acetic acid to give 5-chloro-3-[(4-dimethylamino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (0.32 g), which was dissolved with heating in a mixture of chloroform (10 ml) and ethanol (5 ml). After cooling, to the mixture was added ethanol solution containing hydrogen chloride (about 23 %). The residue obtained by concentration under reduced pressure was recrystallized from a mixture of ethanol (10 ml) and water (0.5 ml) to give colorless crystals of 5-chloro-3-[(4-dimethylamino-1-piperazinyl)carbonylmethyl]-2-benzothiazlinone hydrochloride (0.31 g).

Workup

  1. concentrationconcentrated
  2. additionTo a residue was added saturated sodium carbonate solution
  3. extractionextracted with chloroform
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. concentrationthe solution was concentrated under reduced pressure
  6. washeluted with a mixture of chloroform-methanol (20:1)
  7. additionThe fractions containing the object compound
  8. concentrationconcentrated under reduced pressure
  9. washThe residue was washed with ether

Sources & evidence

ORD record
ord-6319079cd89a4885b61222eebdb56154
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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