Acetic Anhydride → N-[4-methyl-3-(2-phenoxy-ethoxy)-phenyl]-acetamide

HRID 330783노트

반응식

HRID 330783 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:16])=[C:13]([OH:15])[CH:14]=1.Br[C:18]1[CH:19]=[C:20]([O:24][CH2:25][CH3:26])[CH:21]=[CH:22][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(O)(=O)C.CN(C=O)C.O>[CH3:16][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:3])[CH3:2])=[CH:14][C:13]=1[O:15][CH2:26][CH2:25][O:24][C:20]1[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=1

참가 물질

8

반응물 4

HCID 7918Acetic AnhydrideHCID 10796Cesium carbonateHCID 178185-Amino-2-methylphenolHCID 758673-Bromophenetole

생성물 1

HCID 86684778N-[4-methyl-3-(2-phenoxy-ethoxy)-phenyl]-acetamide

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

Acetic anhydride (1.25 mL, 12.2 mmol) was added to a solution of 5-amino-2-methyl phenol (1.0 g, 8.1 mmol) in acetic acid (6 mL), and the reaction was refluxed for 5 mins. Then the reaction mixture was cooled to room temperature and the product was solidified. It was filtered off and washed with water (4 mL) and dried to obtain the product along with the trace amount of O-acylated product. The mixture, to which was added 3-bromophenetole (1.33 g, 6.6 mmol) and Cs2CO3 (2.927 g, 9.0 mmol) in DMF (10 mL), was stirred overnight at 50° C. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined extracts were dried over sodium sulfate and recrystallized from toluene to obtain the pure product 18a in 65% (yield over two steps) as an off-white solid.

후처리

  1. temperaturethe reaction was refluxed for 5 mins
  2. filtrationIt was filtered off
  3. washwashed with water (4 mL)
  4. customdried
  5. customto obtain the product along with the trace amount of O-acylated product
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. dry with materialThe combined extracts were dried over sodium sulfate
  8. customrecrystallized from toluene

출처 및 근거

ORD 기록
ord-904dd1e5c9634532a7bdbe92ef1dfa80
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877752B2

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