Formaldehyde → HCID 21278882, compound

HRID 2291588Notes

Reaction equation

HRID 2291588 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]([NH2:20])[CH2:16][CH2:15]3)=[O:13])[C:6]=2[CH:21]=1.[CH2:22]=O>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[CH2:15][CH2:16][N:17]([N:20]=[CH2:22])[CH2:18][CH2:19]3)=[O:13])[C:6]=2[CH:21]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 212788513-[2-(4-Aminopiperazin-1-yl)-2-oxoethyl]-5-chloro-1,3-benzothiazol-2(3H)-one

Product 1

HCID 21278882HCID 21278882, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-chloro-3-[(4-amino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (5.0 g) and 37% formaldehyde solution (1.38 ml) in acetonitrile (150 ml) was stirred for 1.5 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (50 g) eluting with a mixture of chloroform and methanol (50:1). The fractions containing the desired compound were combined and concentrated under reduced pressure. The residue was recrystallized from ethanol (200 ml) to give colorless crystals of 5-chloro-3-[(4-methyleneamino-1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (5.1 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washeluting with a mixture of chloroform and methanol (50:1)
  3. additionThe fractions containing the desired compound
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol (200 ml)

Sources & evidence

ORD record
ord-22d86a4b059a411e8df0c59cdfc3b3b5
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

Loading…