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

反応式

HRID 732033 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3004171146ff4bd4bf403b0ec1f452cd
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

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