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

HRID 1360903Notes

Reaction equation

HRID 1360903 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-ec668009930d4de5b2d4f4e63d53ceb3
Source dataset
uspto-grants-2011_02
Patent number
US07879888B2

Reaction notes

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