Ethanol → 1-(2,4-Dichlorophenyl)-3-methylurea

HRID 2181618

反応式

HRID 2181618 の反応式
[CH3:1][NH2:2].CCO.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]=[C:15]=[O:16]>C1COCC1>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]([NH:2][CH3:1])=[O:16]

参加物

5

反応物 3

HCID 702EthanolHCID 6329MethylamineHCID 757892,4-Dichlorophenyl isocyanate

生成物 1

HCID 43372531-(2,4-Dichlorophenyl)-3-methylurea収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

A cooled (0° C.) solution of methylamine in EtOH (50 mL, 400 mmol, 8.0 M) in anhydrous THF (300 mL) was treated with 2,4-dichlorophenylisocyanate (25.0 g, 133 mmol). The cooling bath was removed and the mixture was warmed to 65° C. for 20 min. The reaction mixture was then cooled to 0° C. The solid was collected on a Buchner funnel, washed with cold ether, and dried under vacuum to afford N-(2,4-dichlorophenyl)-N′-methyl-urea (21.7 g, 74% yield) as a colorless solid: mp 213.5-214.5° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.17 (d, J=9.2 Hz, 1H), 8.11 (s, 1H), 7.55 (d, J=2.5 Hz, 1H), 7.32 (dd, J=8.8, 2.6 Hz, 1H), 6.91 (d, J=4.8 Hz, 1H), 2.65 (d, J=4.4 Hz, 3H); LRMS (APCI) m/e 259.9 [(M+H+CH3CN)+, calcd for C10H12N3OCl2, 260.0].

後処理

  1. customThe cooling bath was removed
  2. temperatureThe reaction mixture was then cooled to 0° C
  3. customThe solid was collected on a Buchner funnel
  4. washwashed with cold ether
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-aaa9ff9c5f114a54aa9b6f56b903f94e
出典データセット
uspto-grants-2005_05
特許番号
US06894045B2

関連ノート

読み込み中…