Water → 6-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1912607노트

반응식

HRID 1912607 반응식
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[CH:5]=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19](Br)=[O:20].O>CN(C)C=O.C(OCC)(=O)C>[Br:9][C:6]1[CH:5]=[CH:4][C:3]2[O:10][CH2:18][C:19](=[O:20])[NH:1][C:2]=2[C:7]=1[CH3:8]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 595785452-Amino-4-bromo-3-methylphenol

생성물 1

HCID 592815236-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one수율 26.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

An ice cold suspension of 2-amino-4-bromo-3-methylphenol (3.81 g, 18.86 mmol) and potassium carbonate (10.42 g, 75 mmol) in N,N-Dimethylformamide (DMF) (25 mL) was treated by dropwise addition of bromoacetyl bromide (1.971 mL, 22.63 mmol). The mixture was warmed to ambient temperature and stirred for one hour. Water was added and the mixture was diluted with ethyl acetate. There were insoluble solids, so the entire mixture was passed through a fine glass frit to afford 6-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one as an off-white solid (1.20 g, 26%). The filtrate was extracted with ethyl acetate. The extracts were washed with water, then brine, dried over sodium sulfate, filtered and concentrated to give slightly impure 6-bromo-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one as a reddish-brown solid (3.05 g, 67%): 1H NMR (400 MHz, DMSO-d6) δ ppm 10.40 (br. s., 1 H), 7.15 (d, J=8.6 Hz, 1 H), 6.79 (d, J=8.6 Hz, 1 H), 4.50 (s, 2 H), 2.30 (s, 3 H); LC/MS (m/z) ES+=242 (M+1).

출처 및 근거

ORD 기록
ord-13038b633c2a48d198fc7870b5ddeaa0
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609653B2

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