Chlorosuccinimide → HCID 22292769、化合物

HRID 221237ノート

反応式

HRID 221237 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].[Cl:21]N1C(=O)CCC1=O>C(#N)C.O>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:21])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 22292800HCID 22292800、化合物

生成物 1

HCID 22292769HCID 22292769、化合物収率 46.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.900 g, 2.67 mmol) in acetonitrile (30 mL) was treated with N-chlorosuccinimide (0.357 g, 2.67 mmol) and stirred overnight at 70 C. The product mixture was diluted with water (100 mL), extracted twice with EtOAc (100 mL), the combined organic phases washed with brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (20% EtOAc in hexane, silica) resulted in 0.399 g of a clear oil. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.17 (s, 1 H), 6.68 (m, 1 H), 3.88 (s, 3 H), 3.78 (m, 1 H), 3.6-3.3 (m, 2 H), 3.2-2.9 (m, 4 H), 1.34 (m, 3 H). MS calculated for C14H15ClF3NO2+H: 322, observed: 322.

後処理

  1. extractionextracted twice with EtOAc (100 mL)
  2. washthe combined organic phases washed with brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-6e87449a34bf428999d97f627f77f0fd
出典データセット
uspto-grants-2012_06
特許番号
US08207158B2

反応ノート

読み込み中…