Triethylamine → 4-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

HRID 277186ノート

反応式

HRID 277186 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1([CH3:21])[C:13]([N:18]=[C:19]=[O:20])=[CH:14][CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl>[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][C:19](=[O:20])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 145334-Aminophenylacetic acidHCID 691942-Tolyl isocyanate

生成物 1

HCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred mixture of 4-aminophenylacetic acid (15.0 g) and o-tolylisocyanate (10.2 ml) in CH2Cl2 (200 ml) was added triethylamine (13.8 ml). After 1 h the resulting homogeneous solution was concentrated under reduced pressure, dissolved in water (100 ml) and acidified to pH 2 with 1N HCl. The off-white ppt was filtered, suspended in THF (200 ml) and 10 ml conc. HCl was added. The resulting homogeneous solution was concentrated under reduced pressure and recrystallized from EtOAc (800 ml) to give 22 g of the title compound as a white solid. MP 221-20° C.; MS [M+1]+285.2; Analysis calcd. for C16H16N203: C (67.59), H (5.67), N (9.85). Found: C (67.22), H (5.78), N (9.69).

後処理

  1. concentrationAfter 1 h the resulting homogeneous solution was concentrated under reduced pressure
  2. dissolutiondissolved in water (100 ml)
  3. filtrationThe off-white ppt was filtered
  4. addition10 ml conc. HCl was added
  5. concentrationThe resulting homogeneous solution was concentrated under reduced pressure
  6. customrecrystallized from EtOAc (800 ml)

出典と根拠

ORDレコード
ord-d555c2bb91b94b018a94d8c79455fde1
出典データセット
uspto-grants-2002_03
特許番号
US06355662B1

反応ノート

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