Acetic Acid → 3-[(3-Chloropropyl)thio]-4-methyl-5-(tetrahydro-2H-pyran-4-yl)-4H-1,2,4-triazole

HRID 1668559노트

반응식

HRID 1668559 반응식
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:5][NH:4][C:3]1=[S:13].Br[CH2:15][CH2:16][CH2:17][Cl:18].C(O)(=O)C>C(O)C>[Cl:18][CH2:17][CH2:16][CH2:15][S:13][C:3]1[N:2]([CH3:1])[C:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:5][N:4]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 80061-Bromo-3-chloropropaneHCID 692243304-methyl-5-(tetrahydro-2H-pyran-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

생성물 1

HCID 591504903-[(3-Chloropropyl)thio]-4-methyl-5-(tetrahydro-2H-pyran-4-yl)-4H-1,2,4-triazole

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

To 4-methyl-5-(tetrahydro-2H-pyran-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (0.4 g, prepared in analogy to the method described in Preparation 2) in ethanol (6 ml) sodium ethanolate (0.83 ml) was carefully added with stirring followed by 1-bromo-3-chloropropane (0.30 ml). The mixture was heated at 90° C. for 1 h. Acetic acid was added at room temperature until pH=4. After elimination of the solvent under reduced pressure the residue was partitioned between aqueous NaHCO3 (saturated) and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated and submitted to column chromatography (EtOAc—acetone gradient) to give the title compound as white solid (0.173 g).

후처리

  1. additionwas carefully added
  2. customAfter elimination of the solvent under reduced pressure the residue was partitioned between aqueous NaHCO3 (saturated) and DCM
  3. customThe organic layer was collected
  4. extractionthe aqueous phase extracted twice with DCM
  5. concentrationThe combined DCM layers were concentrated

출처 및 근거

ORD 기록
ord-b72219f395234997913c64731b1a4dc8
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989444B2

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