Hydrochloric Acid → N-(2-chloro-3,5-dimethoxyphenyl)acetamide

HRID 58175

反応式

HRID 58175 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:14])[CH3:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Cl.[Cl:16]([O-])(=O)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O>[Cl:16][C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH:11][C:12](=[O:14])[CH3:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 516902Sodium ChlorateHCID 702039N-(3,5-dimethoxyphenyl)acetamide

生成物 1

HCID 56594868N-(2-chloro-3,5-dimethoxyphenyl)acetamide収率 71.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of N-(3,5-dimethoxy-phenyl)-acetamide (5 g, 25.64 mmol) in acetic acid (17 mL) was added 32% aqueous hydrochloric acid solution (14 mL), followed by a solution of sodium chlorate (1.16 g, 11 mmol) in water (1.5 mL) at 0° C. The resulting reaction mixture was stirred for 30 min. at 0° C. Thereafter reaction mixture was poured into ice water and made it basic with K2CO3 powder. The precipitate was filtered off and washed with water. The residue was purified by silica gel column chromatography (Hexane/EtOAc, 88:12) to afford the title compound (1.8 g, 31% of yield) as a white solid. 1HNMR (DMSO-d6, 300 MHz): δ 9.36 (s, 1H), 7.03 (d, 1H), 6.53 (d, 1H), 3.84 (s, 3H), 3.74 (s, 3H), 2.08 (s, 3H); MS (ESI): 230.2 [M+H]+.

後処理

  1. customThe resulting reaction mixture
  2. customThereafter reaction mixture
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customThe residue was purified by silica gel column chromatography (Hexane/EtOAc, 88:12)

出典と根拠

ORDレコード
ord-eab1288e2d1b4eb699d8367c81799a3c
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

関連ノート

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