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

HRID 1360903노트

반응식

HRID 1360903 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ec668009930d4de5b2d4f4e63d53ceb3
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879888B2

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