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

HRID 1912607ノート

反応式

HRID 1912607 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-13038b633c2a48d198fc7870b5ddeaa0
出典データセット
uspto-grants-2013_12
特許番号
US08609653B2

反応ノート

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