Acetic Acid → 6-Iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid

HRID 641965ノート

反応式

HRID 641965 の反応式
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=O)=[CH:9][C:8]([I:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:15](OC)(OC)OC.C(O)(=O)C.[NH2:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[CH3:37])[C:30]([O:32][CH3:33])=[O:31]>C1(C)C=CC=CC=1>[I:14][C:8]1[CH:9]=[C:10]2[C:2](=[C:3]([C:4]([OH:6])=[O:5])[CH:7]=1)[N:1]=[CH:15][N:26]([C:27]1[CH:28]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:34]=[CH:35][C:36]=1[CH3:37])[C:11]2=[O:13]

参加物

6

反応物 4

HCID 176Acetic Acid2 回HCID 9005Trimethyl orthoformate2 回HCID 337778Methyl 3-amino-4-methylbenzoateHCID 670430602-Amino-5-iodoisophthalic acid

生成物 1

HCID 686059086-Iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a suspension 2-amino-5-iodoisophthalic acid (30.4 g) and in toluene (300 ml) was added trimethyl orthoformate (60 ml) followed by acetic acid (5.6 ml). The reaction mixture was stirred at 100° C. for 4 hours when additional trimethyl orthoformate (30 ml) and acetic acid (5.6 ml) was added and the heating continued for a further 21 hours. Methyl 3-amino-4-methylbenzoate (10.9 g) was added and the reaction mixture stirred at 100° C. for 21 hours. The reaction mixture was cooled to room temperature and the resultant solid collected by filtration, washed MeOH and dried in vacuo for 18 hours to yield 6-iodo-3-[5-(methoxycarbonyl)-2-methylphenyl]-4-oxo-3,4-dihydroquinazoline-8-carboxylic acid as a white solid (21.1 g); NMR Spectrum: (DMSOd6) 2.20 (s, 3H), 3.85 (s, 3H), 7.61 (d, 1H), 8.02 (m, 1H), 8.08 (s, 1H), 8.54 (m, 1H), 8.62 (m, 2H); Mass Spectrum: M+H+ 465.

後処理

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe resultant solid collected by filtration
  4. washwashed MeOH
  5. customdried in vacuo for 18 hours

出典と根拠

ORDレコード
ord-04a50319fa4c490abc0e8598e7b88059
出典データセット
uspto-grants-2010_04
特許番号
US07696215B2

反応ノート

読み込み中…