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

HRID 58175

반응식

HRID 58175 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-eab1288e2d1b4eb699d8367c81799a3c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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