1-Fluoro-2-nitrobenzene → 2-Methyl-5-(2-nitro-phenylamino)-thiazole-4-carboxylic acid ethyl ester

HRID 1350442ノート

反応式

HRID 1350442 の反応式
[NH2:1][C:2]1[S:6][C:5]([CH3:7])=[N:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].O.[OH-].[Li+]>CS(C)=O>[CH2:11]([O:10][C:8]([C:3]1[N:4]=[C:5]([CH3:7])[S:6][C:2]=1[NH:1][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21])=[O:9])[CH3:12]

参加物

5

反応物 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 13329095Ethyl 5-amino-2-methylthiazole-4-carboxylate

生成物 1

HCID 543485952-Methyl-5-(2-nitro-phenylamino)-thiazole-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Add a solution of ethyl 5-amino-2-methylthiazole-4-carboxylate (120 g; 645 mmol) and 2-fluoronitrobenzene (68 mL; 645 mmol) in dimethylsulphoxide (1 L) to a 2 L 3-necked RB flask equipped with reflux condenser, thermometer, mechanical stirrer. Add lithium hydroxide monohydrate (54 g; 1290 mmol) to the solution and heat at 50° C. for 3 hours under nitrogen. Cool the purple solution and pour onto ice/water, allow to stir for one hour, filter and wash with water, dry at 50° C. under reduced pressure to give 190 g (96%) as an orange solid: mass spectrum (m/e): 308 (M+1); 1HNMR(300 MHz, DMSO, ppm): 1.25 (tr, 3H), 2.56 (s, 3H), 4.25 (q, 2H), 7.20 (m, 1H), 7.78 (m, 2H), 8.20 (d, 1H), 11.42 (s, 1H, NH). 13CNMR(75 MHz, DMSO, ppm): 24.4, 29.2, 71.2, 127.8, 132.5, 132.8, 137.8, 146.5, 147.0, 147.5, 160.2, 161.5, 173.7. Formula: C13H13N3O4S.

後処理

  1. customequipped
  2. temperaturewith reflux condenser
  3. temperatureCool the purple solution
  4. additionpour onto ice/water
  5. filtrationfilter
  6. washwash with water
  7. customdry at 50° C. under reduced pressure
  8. customto give 190 g (96%) as an orange solid

出典と根拠

ORDレコード
ord-81767743cb2b4418b7c683bde55824c9
出典データセット
uspto-grants-2007_05
特許番号
US07214673B2

反応ノート

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