N-(5-Chloro-2-methoxyphenyl)thiourea → N-(2-(5-Chloro-2-methoxyphenylamino)-4,5'-bithiazol-2'-yl)pivalamide

HRID 1942995ノート

反応式

HRID 1942995 の反応式
Br[CH2:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)=O.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([NH:24][C:25]([NH2:27])=[S:26])[CH:23]=1>CCO>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([O:28][CH3:29])=[C:22]([NH:24][C:25]2[S:26][CH:2]=[C:3]([C:5]3[S:9][C:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=3)[N:27]=2)[CH:23]=1

参加物

4

反応物 2

HCID 2732660N-(5-Chloro-2-methoxyphenyl)thioureaHCID 25130826N-(5-(2-Bromoacetyl)thiazol-2-yl)pivalamide

生成物 1

HCID 25130491N-(2-(5-Chloro-2-methoxyphenylamino)-4,5'-bithiazol-2'-yl)pivalamide収率 84%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of 21z (0.73 g, 2.3 mmol) and N-(5-chloro-2-methoxyphenyl)thiourea (0.73 g, 2.53 mmol) in EtOH (25 mL) was refuxed for 30 min. Upon cooling, the product was collected by filtration and washed with cold ethanol to yield 22z as a pale yellow solid (0.40 g, 84%). Mp decomposition at 216° C. 1H NMR (600 MHz, DMSO-d6): δ 11.86 (br s, 1H) 9.93 (br s, 1H), 8.64 (d, J=2.4 Hz, 1H), 7.83 (s, 1H), 7.18 (s, 1H), 7.02 (d, J=8.4 Hz, 1H), 6.98 (dd, J=8.4 Hz, 2.4 Hz, 1H), 3.86 (s, 3H), 1.25 (s, 9H). 13C NMR (150 MHz, DMSO-d6): δ 176.7, 162.1, 158.9, 146.6, 140.2, 136.4, 130.5, 124.7, 124.2, 121.3, 117.3, 112.1, 91.0, 56.1, 38.8, 26.6. HRMS m/z (ESI) calcd. for C18H19ClN4O2S2 (M+H)+ 423.0711. Found 423.0713.

後処理

  1. temperatureUpon cooling
  2. filtrationthe product was collected by filtration
  3. washwashed with cold ethanol

出典と根拠

ORDレコード
ord-13875481471948a38197ae3ab5b2e260
出典データセット
uspto-grants-2013_03
特許番号
US08389736B2

反応ノート

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