Formic Acid → HCID 66987301、化合物

HRID 555273ノート

反応式

HRID 555273 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][OH:13])=[C:6]([NH2:14])[CH:5]=1.[CH:16](O)=O>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][OH:13])[CH:16]=[N:14][C:6]=2[CH:5]=1)=[O:15]

参加物

3

反応物 2

HCID 284Formic Acid2 回HCID 51358181HCID 51358181、化合物

生成物 1

HCID 66987301HCID 66987301、化合物収率 78%

反応条件

温度
45 °C

実験手順

3-Amino-4-(2-hydroxy-ethylamino)-benzoic acid methyl ester (2.6 g, 12.0 mmol) was dissolved in formic acid (20 mL). The solution was heated at 45° C. for 1 h. After checking the completion of reaction by TLC, formic acid was evaporated at <40° C. under reduced pressure and the resulting solid was recrystallized from EtOAc. The above solid was dissolved in 3N HCl, stirred at ambient temperature for 1 h, basified back with saturated sodium bicarbonate solution and extracted with EtOAc. The organic layer was evaporated to give 2.1 g (78%) of 1-(2-hydroxy-ethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 221 (M+1): 1H NMR (300 MHz, DMSO-d6) δ 3.7 (q, 2H), 3.9 (s, 3H), 4.3 (t, 3H), 5.0 (t, 1H), 7.7 (d, 1H), 7.9 (dd, 1H), 8.25 (s, 1H), 8.35 (s, 1H)

後処理

  1. customwas evaporated at <40° C. under reduced pressure
  2. customthe resulting solid was recrystallized from EtOAc
  3. dissolutionThe above solid was dissolved in 3N HCl
  4. extractionextracted with EtOAc
  5. customThe organic layer was evaporated

出典と根拠

ORDレコード
ord-6344907218d44c418049a5ed578ea07f
出典データセット
uspto-grants-2011_11
特許番号
US08053431B2

反応ノート

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