Chloroacetyl chloride → 8-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 470985노트

반응식

HRID 470985 반응식
Cl[CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[C:8]([OH:24])=[C:9]([C:21](=[O:23])[CH3:22])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:21]([C:9]1[C:8]2[O:24][CH2:2][C:3](=[O:4])[NH:6][C:7]=2[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:23])[CH3:22]

참가 물질

6

반응물 4

HCID 6577Chloroacetyl chlorideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

생성물 1

HCID 579889708-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

2-Chloroacetyl chloride (1.8 mL) was added dropwise to a stirred mixture of 1-(3-amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone (example 11, step c) (5.2 g) and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for 2 h. Cesium carbonate (7.90 g) was added and the mixture heated at 100° C. for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2×200 mL), washed with water (3×300 mL) and brine, dried over anhydrous sodium sulphate, filtered and evaporated under vacuum. The solid residue was treated with diethyl ether, filtered and dried to afford the subtitled compound as a beige solid. Yield 5.7 g.

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. customquenched with water (500 mL)
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. washwashed with water (3×300 mL) and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. additionThe solid residue was treated with diethyl ether
  9. filtrationfiltered
  10. customdried

출처 및 근거

ORD 기록
ord-2245209a3ae342e59b432295b548beae
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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