Thiobenzamide → 2-phenyl-4H,5H,6H,7H-(1,3)thiazolo(5,4-c)pyridine

HRID 585495Notes

Reaction equation

HRID 585495 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10](Br)[CH2:9]1)=O)(C)(C)C.[C:16]([NH2:24])(=[S:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[C:17]1([C:16]2[S:23][C:10]3[CH2:9][NH:8][CH2:13][CH2:12][C:11]=3[N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 683563ThiobenzamideHCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

Product 1

HCID 223374872-phenyl-4H,5H,6H,7H-(1,3)thiazolo(5,4-c)pyridineYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-tert-butoxycarbonyl-3-bromopiperidin-4-one (8 g) and thiobenzamide (3.4 g) in DMF was heated at 70° C. for 16 h, then cooled to room temperature. The solvent was evaporated in vacuo and the residue dissolved in water (100 ml) and washed with ether (100 ml), then basified with sodium hydroxide and extracted into ethyl acetate (3×100 ml). The solvent was dried (MgSO4) and evaporated to give the title compound as cream solid (2.81 g, 53% based on thiobenzamide used).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in water (100 ml)
  3. washwashed with ether (100 ml)
  4. extractionextracted into ethyl acetate (3×100 ml)
  5. dry with materialThe solvent was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c3b2a1641c434932972fdce5c36ef893
Source dataset
uspto-grants-2005_08
Patent number
US06933306B2

Reaction notes

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