Chloroacetyl chloride → 8-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 2175217노트

반응식

HRID 2175217 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[OH:9].C(=O)(O)[O-].[Na+].Cl[CH2:16][C:17](Cl)=[O:18]>C(#N)C.O.CCOC(C)=O>[Br:8][C:4]1[C:3]2[O:9][CH2:16][C:17](=[O:18])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 155315062-Amino-6-bromophenol

생성물 1

HCID 218735338-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one수율 94%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 2-amino-6-bromophenol (1 g, 5.32 mmol) in acetonitrile (10 mL) and water (10 mL) was added sodium bicarbonate (1.028 g, 12.23 mmol). The mixture was cooled to 0° C. and chloroacetyl chloride (0.554 mL, 6.91 mmol) was added dropwise. The reaction was refluxed overnight. After cooling to room temperature, the mixture was diluted with EtOAc, washed with water, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (1.14 g, 94% yield) as a dark brown solid. 1H NMR (400 MHz, CDCl3) δ 8.22 (br. s, 1H), 7.23 (dd, J=8.0, 1.4 Hz, 1H), 6.86 (t, J=8.0 Hz, 1H), 6.76 (dd, J=7.9, 1.3 Hz, 1H), 4.74 (s, 2H).

후처리

  1. temperatureThe reaction was refluxed overnight
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b3380e3769174ad9b564c6279e138203
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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