2-[3-sulfanyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-4-yl]acetic acid → 4-(2-Hydroxy-ethyl)-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione

HRID 732033

반응식

HRID 732033 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]1[N:16]([CH2:17][C:18](O)=[O:19])[C:15](=[S:21])[NH:14][N:13]=1>C1COCC1>[OH:19][CH2:18][CH2:17][N:16]1[C:12]([C:8]2[S:7][CH:11]=[CH:10][CH:9]=2)=[N:13][NH:14][C:15]1=[S:21]

참가 물질

4

반응물 2

HCID 49625532-[3-sulfanyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-4-yl]acetic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 859371364-(2-Hydroxy-ethyl)-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a slurry of LAH (38.1 mg, 1.00 mmol) in anhydrous THF (8 ml) was drop wise added (3-thiophen-2-yl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-acetic acid (101 mg, 0.42 mmol) in anhydrous THF (4 ml). The mixture was reacted for 2 h and then quenched with saturated aq. Na2SO4 (10 ml). THF was removed under reduced pressure and the residue was made acidic with aq. HCl (3N) and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine (15 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product was used without purification in the next step. 1H NMR (DMSO-d6), δ (ppm): 13.94 (s, 1H), 7.86 (d, 1H); 7.81 (d, 1H), 7.24 (dd, 1H), 5.09 (t, 1H), 4.16 (t, 2H), 3.76 (app. q, 2H).

후처리

  1. customThe mixture was reacted for 2 h
  2. customquenched with saturated aq. Na2SO4 (10 ml)
  3. customTHF was removed under reduced pressure
  4. custompartitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted with EtOAc (3×20 ml)
  6. washThe combined organic layers were washed with brine (15 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was used without purification in the next step

출처 및 근거

ORD 기록
ord-3004171146ff4bd4bf403b0ec1f452cd
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585881B2

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