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

HRID 641965노트

반응식

HRID 641965 반응식
[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]

참가 물질

6

반응물 4

HCID 176Acetic Acid2회HCID 9005Trimethyl orthoformate2회HCID 337778Methyl 3-amino-4-methylbenzoateHCID 670430602-Amino-5-iodoisophthalic acid

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-04a50319fa4c490abc0e8598e7b88059
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696215B2

반응 노트

불러오는 중…