2,5-Dibromoterephthalic acid → 2,5-Dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid

HRID 1943661ノート

反応式

HRID 1943661 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4]([OH:6])=O.BrC1C=C(C(Cl)=O)C(Br)=CC=1C(Cl)=O.[O:29]1[CH2:34][CH2:33][NH:32][C:31]2[CH:35]=[N:36][CH:37]=[CH:38][C:30]1=2>CN(C)C=O.S(Cl)(Cl)=O.ClCCl.C(N(CC)CC)C>[Br:14][C:8]1[CH:7]=[C:3]([C:4]([N:32]2[CH2:33][CH2:34][O:29][C:30]3[CH:38]=[CH:37][N:36]=[CH:35][C:31]2=3)=[O:6])[C:2]([Br:1])=[CH:10][C:9]=1[C:11]([OH:13])=[O:12]

参加物

8

反応物 3

HCID 836902,5-Dibromoterephthalic acidHCID 218859502H,3H,4H-pyrido[4,3-b][1,4]oxazineHCID 229969282,5-Dibromobenzene-1,4-dicarbonyl dichloride

生成物 1

HCID 446088742,5-Dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide触媒HCID 8471Triethylamine触媒HCID 6344Dichloromethane溶媒2 回HCID 24386Thionyl Chloride溶媒

実験手順

In a 20 ml flask, 2,5-dibromo-terephthalic acid (100 mg, 0.31 mmol) and N,N-dimethyl formamide (3 drops) were dissolved in thionyl chloride (2 ml). After stirring for 2 hours at 800, the reaction mixture was cooled to room temperature and concentrated. Crude 2,5-dibromo-terephthaloic dichloride (112 mg, 0.31 mmol) was dissolved in dichloromethane (6 ml) and was added to 3,4-dihydro-2H-pyrido[4,3-b][1,4]oxazine (20.9 mg, 0.15 mmol) dissolved in dichloromethane (1 ml). Triethylamine (3 drops) were slowly added thereto and stirred at room temperature for 16 hours. After completion of the reaction, the residue was purified by preparative LC/Mass to obtain the target compound 23, i.e., 2,5-dibromo-4-(2,3-dihydro-pyrido[4,3-b][1,4]oxazin-4-carbonyl)-benzoic acid, as white solid (23 mg, 5%).

後処理

  1. concentrationconcentrated
  2. stirringstirred at room temperature for 16 hours
  3. customAfter completion of the reaction
  4. customthe residue was purified by preparative LC/Mass

出典と根拠

ORDレコード
ord-1c2ed47af75544758399639936b77033
出典データセット
uspto-grants-2013_03
特許番号
US08394792B2

反応ノート

読み込み中…