Hydrochloric Acid → 4-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one

HRID 924861ノート

反応式

HRID 924861 の反応式
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:26][CH2:27][CH3:28])[C:24]=1[OH:25])[CH:20]=O.[NH2:29][C:30]([NH2:32])=[O:31].Cl>CCO>[Br:16][C:17]1[CH:18]=[C:19]([CH:20]2[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:22]=[C:23]([O:26][CH2:27][CH3:28])[C:24]=1[OH:25]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

生成物 1

HCID 569614644-(3-bromo-5-ethoxy-4-hydroxyphenyl)-5,6-diphenyl-3,4-dihydropyrimidin-2(1H)-one収率 11.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 1,2-diphenylethanone (4.80 g, 25 mmol), 3-bromo-5-ethoxy-4-hydroxybenzaldehyde (5.00 g, 20 mmol) and urea (3.68 g, 61 mmol) in EtOH (250 mL) was added conc. HCl (10 mL). The mixture was heated at reflux for 112 h. Followed standard aqueous workup procedure and purified by silica gel column chromatography (PE:EA=1:3) to afford Compound 100 as a white solid (1.06 g, 11%). 1H NMR (MeOH-d4 500 MHz TMS): δ 7.24 (s, 5H), 7.09 (s, 1H), 7.04 (s, 3H), 6.85 (s, 3H), 5.17 (s, 1H), 4.03 (m, 2H), 1.37 (t, J=7.5 Hz, 3H); MS (ESI): m/z 465.0 [M+1]+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 112 h
  3. customFollowed standard aqueous workup procedure and purified by silica gel column chromatography (PE:EA=1:3)

出典と根拠

ORDレコード
ord-a4e74acbca494c2480b1ba2fe5d85dc0
出典データセット
uspto-grants-2016_03
特許番号
US09283229B2

反応ノート

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