Sodium hydride → HCID 72429334、化合物

HRID 349609

反応式

HRID 349609 の反応式
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[H-].[Na+].[Cl:18][CH:19]=[CH:20][CH2:21]Cl>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[N:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:21][CH:20]=[CH:19][Cl:18]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 3571360N-(tert-Butoxycarbonyl)-2-bromoaniline

生成物 1

HCID 72429334HCID 72429334、化合物収率 89.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A solution of 3.2 (350 mg, 1.29 mmol) in DMF (7 ml) was cooled to 0° C. and NaH (93 mg, 3.85 mmol) was added. The resulting mixture was stirred for 15 mins and 1,3 dichloropropene (358 μl, 3.85 mmol) was added. The mixture was allowed to warm to 25 ° C. and stirred for 15 h. The mixture was then concentrated. H2O (10 ml) was added to the residue and the solution was extracted with EtOAc (3×10 ml). The combined organic layers were dried with MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9) to afford 3.3 (400 mg, 89%) as a pale yellow oil. FABMS (NBA/NaI) 346 (M+H+ expected 346).

後処理

  1. stirringstirred for 15 h
  2. concentrationThe mixture was then concentrated
  3. additionH2O (10 ml) was added to the residue
  4. extractionthe solution was extracted with EtOAc (3×10 ml)
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9)

出典と根拠

ORDレコード
ord-524453802d4c4ea4bede5730af445a25
出典データセット
uspto-grants-2007_02
特許番号
US07179921B2

関連ノート

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