Dimethylformamide → HCID 21278869, compound

HRID 2291580Notes

Reaction equation

HRID 2291580 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:10])=O)[C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[S:3]1.O[N:16]1[C:20](=O)[CH2:19][CH2:18][C:17]1=O.C[N:24](C)C=O>>[N:16]1([C:8]([CH2:7][N:6]2[C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=3[S:3][C:2]2=[O:1])=[O:10])[CH2:20][CH2:19][NH:24][CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 80170N-HydroxysuccinimideHCID 704583(2-oxo-1,3-benzothiazol-3(2H)-yl)acetic acid

Product 1

HCID 21278869HCID 21278869, compound

Procedure

To an ice-cooled solution of 2-oxo-3-benzothiazolineacetic acid [J. Prakt. Chem. 27 (3-4), 220-4 (1965); 8.1 g] and N-hydroxysuccinimide (5.4 g) in N,N-dimethylformamide (50 ml) was gradually added N,N-dicyclohexylcarbodiimide (9.6 g), and the mixture was stirred for an hour at ambient temperature. The dicyclohexylurea that precipitated from the reaction mixture was filtered off. To a stirred solution of piperazine (16.7 g) in N,N-dimethylformamide (200 ml) was added dropwise the filtrate for a period of 40 minutes below 20° C. The final mixture was stirred for 3.5 hours at ambient temperature and then filtered. The filtrate was concentrated under reduced pressure. The residue was dissolved in 2N hydrochloric acid and the solution was washed with chloroform. The aqueous layer was adjusted to pH 9 with an aqueous solution of sodium hydrogen carbonate, and the turbid solution was extracted with chloroform (80 ml×3). The extracts were combined and dried over magnesium sulfate. After evaporation of the solvent, 3-[(1-piperazinyl)carbonylmethyl]-2-benzothiazolinone (9.50 g) was obtained as white powders.

Workup

  1. customThe dicyclohexylurea that precipitated from the reaction mixture
  2. filtrationwas filtered off
  3. additionTo a stirred solution of piperazine (16.7 g) in N,N-dimethylformamide (200 ml) was added dropwise the filtrate for a period of 40 minutes below 20° C
  4. stirringThe final mixture was stirred for 3.5 hours at ambient temperature
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in 2N hydrochloric acid
  8. washthe solution was washed with chloroform
  9. extractionthe turbid solution was extracted with chloroform (80 ml×3)
  10. dry with materialdried over magnesium sulfate
  11. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-037f6615111f4c0ea93526a7a21f6551
Source dataset
uspto-grants-1989_01
Patent number
US04797399

Reaction notes

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