Chlorosuccinimide → N-[5-(2-chloro-3-thienyl)-4-methyl-1,3-thiazol-2-yl]acetamide

HRID 1948446Notes

Reaction equation

HRID 1948446 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:12][C:13](=[O:15])[CH3:14])[S:5][C:6]=1[C:7]1[CH:11]=[CH:10][S:9][CH:8]=1.[Cl:16]N1C(=O)CCC1=O>C(#N)C>[Cl:16][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[C:6]1[S:5][C:4]([NH:12][C:13](=[O:15])[CH3:14])=[N:3][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11993592N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamide

Product 1

HCID 86652448N-[5-(2-chloro-3-thienyl)-4-methyl-1,3-thiazol-2-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

N-[4-methyl-5-(3-thienyl)-1,3-thiazol-2-yl]acetamide, prepared as in Step I of Example 23 (600 mg; 2.52 mmol; 1 eq) is dissolved in ACN (20 ml) in presence of 100 μl of HClO4 at room temperature. A solution of N-chlorosuccinimide (369.8 mg; 2.77 mmol; 1.10 eq) in ACN (2 ml) is added slowly at room temperature over a period of one hour. Reaction mixture is stirred at room temperature for 1 night before being quenched with water (1 ml). It is then concentrated under vacuo and expected compound extracted with EtOAc, washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, ACN (5 ml) is added, affording after precipitation, the title compound as a solid (600 mg; 95%).

Workup

  1. customReaction mixture
  2. custombefore being quenched with water (1 ml)
  3. concentrationIt is then concentrated under vacuo and expected compound
  4. extractionextracted with EtOAc
  5. washwashed with NH4Cl saturated solution, water
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of the solvents, ACN (5 ml)
  8. additionis added
  9. customaffording
  10. customafter precipitation

Sources & evidence

ORD record
ord-1fdbc68bc7c248a1b4892f797b0a94ca
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

Loading…