Acetic Anhydride → HCID 14423126, compound

HRID 476571Notes

Reaction equation

HRID 476571 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]3)=[O:13])[C:9](=[O:23])[S:8][C:5]2=[N:6][CH:7]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:24](=[O:26])[CH3:25])[CH2:16][CH2:15]3)=[O:13])[C:9](=[O:23])[S:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14423121HCID 14423121, compound

Product 1

HCID 14423126HCID 14423126, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cooled solution of 6-chloro-2-oxo-1-{[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl]-1,2-dihydrothiazolo[5,4-b]pyridine (1.35 g) in dry pyridine (10 ml), acetic anhydride (0.73 g) was added dropwise and then the mixture was stirred at the temperature for 2 hours and at the room temperature for 4 hours. After removal of the solvent, the residual oil obtained was purified on an aluminum-oxide column chromatography using a mixture of chloroform and n-hexane (2:1). The fractions containing the objective compound were collected and evaporated to give crude crystals. The crude crystals were recrystallized from ethyl acetate to afford 6-chloro-2-oxo-1-{[4-(2-acetoxyethyl)-1-piperazinyl]carbonylmethyl}-1,2-dihydrothiazolo[5,4-b]pyridine (1,2 g).

Workup

  1. additionwas added dropwise
  2. customAfter removal of the solvent
  3. customthe residual oil obtained
  4. customwas purified on an aluminum-oxide column chromatography
  5. additiona mixture of chloroform and n-hexane (2:1)
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated
  9. customto give crude crystals
  10. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-aa805ceb73cf4fb68a4d6823a736590d
Source dataset
uspto-grants-1989_12
Patent number
US04885297

Reaction notes

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