Methanol → 4,4'-Bis(4-aminobenzamido)-3,3'-dihydroxybiphenyl

HRID 2396867

反応式

HRID 2396867 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([OH:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C([N:19]([CH2:22][CH3:23])CC)C.[N+:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)([O-])=O.[CH3:36][OH:37]>O1CCCC1.CN(C)C=O>[NH2:24][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([NH:8][C:36](=[O:37])[C:2]4[CH:3]=[CH:23][C:22]([NH2:19])=[CH:6][CH:7]=4)=[C:2]([OH:1])[CH:3]=3)=[CH:10][C:11]=2[OH:16])=[O:32])=[CH:29][CH:28]=1

参加物

7

反応物 4

HCID 887MethanolHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 169183,3'-Dihydroxybenzidine

生成物 1

HCID 189864474,4'-Bis(4-aminobenzamido)-3,3'-dihydroxybiphenyl収率 99.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

35.0 g (0.162 moles) of 3,3'-dihydroxy-4,4'-diaminobiphenyl and 36.0 g (0.356 moles) of triethylamine were dissolved in a mixed solvent of 300 ml of tetrahydrofuran and 300 ml of N,N-dimethylformamide (DMF) and cooled down to 0° C. Thereafter, a solution of 63.1 g (0.340 moles) of p-nitrobenzoyl chloride in 150 ml of tetrahydrofuran was dropped in the solution in such a way that the resultant reaction solution had a temperature not higher than 10° C. Subsequently, the reaction solution was poured into one liter of methanol thereby permitting the resulting reaction product to be precipitated, followed by filtering, washing with tetrahydrofuran, then with water and finally with methanol, and drying to obtain crude red crystals of 4,4'-bis(4-aminobenzamido)-3,3'-dihydroxybiphenyl. The yield was 82.1 g (at a yield of 99.7%). The crude crystals were recrystallized from a mixed solvent of dimethylformamide and methanol to obtain a pure product.

後処理

  1. customreaction solution
  2. customhigher than 10° C
  3. customthe resulting reaction product
  4. customto be precipitated
  5. filtrationby filtering
  6. washwashing with tetrahydrofuran
  7. dry with materialwith water and finally with methanol, and drying

出典と根拠

ORDレコード
ord-360cd188f6e5401f8bc5216d044f15d7
出典データセット
uspto-grants-1996_02
特許番号
US05494991

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