1-Methyl-3-pyrrolidinol → 3-Butoxy-4-(1-methyl-pyrrolidin-3-yloxy)-[1,2,5]thiadiazole

HRID 399651

反応式

HRID 399651 の反応式
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3]1.C([Li])CCC.[CH2:13]([O:17][C:18]1[C:22](S(C)(=O)=O)=[N:21][S:20][N:19]=1)[CH2:14][CH2:15][CH3:16]>C1COCC1.CCCCCC>[CH2:13]([O:17][C:18]1[C:22]([O:7][CH:4]2[CH2:5][CH2:6][N:2]([CH3:1])[CH2:3]2)=[N:21][S:20][N:19]=1)[CH2:14][CH2:15][CH3:16]

参加物

6

反応物 3

HCID 930741-Methyl-3-pyrrolidinolHCID 196003073-Butyloxy-4-methanesulfonyl-1,2,5-thiadiazoleHCID 178418339Butyllithium

生成物 1

HCID 108250553-Butoxy-4-(1-methyl-pyrrolidin-3-yloxy)-[1,2,5]thiadiazole

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

A solution of 1-methyl-3-pyrrolidinol (0.6 g, 0.0059 mol) in THF (20 mL) was treated with 1.6M n-butyllithium in hexane (3.1 mL), 0.005 mol). To the solution was added 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1.0 g, 0.0042 mol) and the reaction heated to reflux overnight. The solvent was evaporated, the residue acidified with cold 1N HCl, and the mixture extracted with ether. The aqueous fraction was made basic, extracted with EtOAc, and the extracts washed with water. The extracts were dried and the solvent evaporated to give a liquid. The HCl salt (0.7 g) crystallized from EtOAc, m.p. 157°-158° C. (Compound 28).

後処理

  1. temperaturethe reaction heated
  2. temperatureto reflux overnight
  3. customThe solvent was evaporated
  4. extractionthe mixture extracted with ether
  5. extractionextracted with EtOAc
  6. washthe extracts washed with water
  7. customThe extracts were dried
  8. customthe solvent evaporated
  9. customto give a liquid
  10. customThe HCl salt (0.7 g) crystallized from EtOAc, m.p. 157°-158° C. (Compound 28)

出典と根拠

ORDレコード
ord-2d543bad95ac4462a725dd39cd12bf83
出典データセット
uspto-grants-1998_10
特許番号
US05821370

関連ノート

読み込み中…