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Triethylamine → 4-Acetyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-1-naphthalenecarboxamide

HRID 1037796
ノート
印刷プレビュー

反応式

HRID 1037796 の反応式
[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([F:10])([F:9])[F:8])=[O:4].[C:11]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24](Cl)=[O:25])=[CH:16][CH:15]=1)(=[O:13])[CH3:12].C(N(CC)CC)C>ClCCCl>[C:11]([C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]([NH:1][CH2:2][C:3](=[O:4])[NH:5][CH2:6][C:7]([F:10])([F:9])[F:8])=[O:25])=[CH:16][CH:15]=1)(=[O:13])[CH3:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 866498014-Acetyl-1-naphthalenecarbonyl chloride

生成物 1

HCID 668651914-Acetyl-N-(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-1-naphthalenecarboxamide収率 75%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒3 回

反応条件

温度
25 °C

実験手順

A solution of 2-amino-N-(2,2,2-trifluoroethyl)acetamide (21.90 g, 0.14 mol) in 1,2-dichloroethane (80 mL) was added dropwise over 15 min to a solution of the product of Example 7, Step A (32.50 g, 0.14 mol) in 1,2-dichloroethane (160 mL) at a temperature of 25 to 30° C. The resulting mixture was further stirred for 10 min at 25° C. A solution of triethylamine (14.20 g, 0.14 mol) in 1,2-dichloroethane (80 mL) was then added dropwise over 44 min at 25° C., and the mixture was stirred further for 20 min at 25° C. The solvent was removed under reduced pressure, and the residue was dissolved in hot acetonitrile (50 mL). The mixture was then cooled to 25° C., and water (40 mL) was added dropwise. The mixture was further cooled to 0° C. and filtered. The isolated solid was washed with water (100 mL) and dried overnight in a vacuum oven (approximately 16-33 kPa at 50° C.) to provide the title product as an off-white solid (37 g, 75% yield) melting at 169-169° C.

後処理

  1. stirringthe mixture was stirred further for 20 min at 25° C
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in hot acetonitrile (50 mL)
  4. temperatureThe mixture was then cooled to 25° C.
  5. additionwater (40 mL) was added dropwise
  6. temperatureThe mixture was further cooled to 0° C.
  7. filtrationfiltered
  8. washThe isolated solid was washed with water (100 mL)
  9. customdried overnight in a vacuum oven (approximately 16-33 kPa at 50° C.)

出典と根拠

ORDレコード
ord-f1e41d41f8d643aea9a2e03aaa85f42a
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546618B2

反応ノート

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