Methanesulfonic Acid → 1-Ethyl-3-[5-hydroxy-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea

HRID 712153ノート

反応式

HRID 712153 の反応式
C([O:8][C:9]1[CH:10]=[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)C1C=CC=CC=1.CS(O)(=O)=O>C(Cl)Cl.CCOCC>[CH2:21]([NH:20][C:18]([NH:17][C:15]1[S:16][C:12]2[C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:10][C:9]([OH:8])=[CH:23][C:13]=2[N:14]=1)=[O:19])[CH3:22]

参加物

5

反応物 2

HCID 6395Methanesulfonic AcidHCID 727246171-[5-Benzyloxy-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea

生成物 1

HCID 727246181-Ethyl-3-[5-hydroxy-7-(2-pyridyl)-1,3-benzothiazol-2-yl]urea収率 97%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 1-[5-benzyloxy-7-(2-pyridyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea (76 g, 0.187 mol) in DCM (1.7 L) was added methane sulfonic acid (270 mL, 4.17 mol) dropwise over 30 min. The reaction mixture was then stirred at rt for 3 h. After the completion of reaction (by TLC), the reaction mass was concentrated under reduced pressure. EtOAc (1 L) was added to the residue and the solution poured carefully onto crushed ice. The pH of the solution was maintained to 8-9 by addition of saturated NaHCO3 solution followed by extraction with EtOAc (3×5 L). The combined organics were washed with water, brine, dried (anhydrous Na2SO4), filtered and concentrated under reduced pressure. The residue thus obtained was stirred in Et2O (1.0 L) for 1 h at rt then filtered to obtain the desired product (57.0 g, 97%). 1H-NMR (DMSO-d6): δ 1.08 (t, J=7.20 Hz, 3H), 3.20 (m, 2H), 6.86 (br s, 1H), 7.0 (s, 1H), 7.46 (s, 2H), 7.96 (m, 1H), 8.10 (m, 1H), 8.76 (m, 1H), 9.59 (br s, 1H) and 10.41 (br s, 1H). LCMS: 315.06 [M+H]+.

後処理

  1. customAfter the completion of reaction (by TLC)
  2. concentrationthe reaction mass was concentrated under reduced pressure
  3. additionEtOAc (1 L) was added to the residue
  4. additionthe solution poured carefully
  5. customonto crushed ice
  6. temperatureThe pH of the solution was maintained to 8-9 by addition of saturated NaHCO3 solution
  7. extractionfollowed by extraction with EtOAc (3×5 L)
  8. washThe combined organics were washed with water, brine
  9. dry with materialdried (anhydrous Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue thus obtained
  13. filtrationthen filtered

出典と根拠

ORDレコード
ord-3864ffe345124098a2ee75d4e98bf9ef
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

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