Diisopropylethylamine → HCID 178509206、化合物

HRID 38750ノート

反応式

HRID 38750 の反応式
[C:1]([NH:4][NH2:5])(N)=[NH:2].Cl.[CH:7]1([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([N:20]=[C:21]=[S:22])=[CH:12][CH:11]=2)[CH2:9][CH2:8]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH2:2][C:1]1[N:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([CH:7]3[CH2:9][CH2:8]3)=[CH:11][CH:12]=2)[C:21]([SH:22])=[N:5][N:4]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 565954581-Cyclopropyl-4-isothiocyanatonaphthaleneHCID 178418668HCID 178418668、化合物

生成物 1

HCID 178509206HCID 178509206、化合物収率 50.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of aminoguanidine hydrochloride (3.18 g, 29 mmol), 1-cyclopropyl-4-isothiocyanato naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50° C. for 15 hours. The solvent was removed under reduced pressure, toluene added, and the solvent was evaporated again. Sodium hydroxide solution (2M, 30 mL) was added and the reaction mixture heated at 50° C. for 60 hours. The reaction mixture was filtered and the filtrate neutralized with aqueous HCl (2M). The mixture was re-filtered and the solvent removed under reduced pressure. The residue was purified by silica gel chromatography to yield 5-amino-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazole-3-thiol (2.0 g, 49%).

後処理

  1. customThe solvent was removed under reduced pressure, toluene
  2. additionadded
  3. customthe solvent was evaporated again
  4. additionSodium hydroxide solution (2M, 30 mL) was added
  5. temperaturethe reaction mixture heated at 50° C. for 60 hours
  6. filtrationThe reaction mixture was filtered
  7. filtrationThe mixture was re-filtered
  8. customthe solvent removed under reduced pressure
  9. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-798a34466854460c85da1132c6762a24
出典データセット
uspto-grants-2013_09
特許番号
US08524754B2

反応ノート

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