Triethylamine → HCID 54481087、化合物

HRID 359661

反応式

HRID 359661 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([OH:23])(=O)[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.[NH2:25][CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=1.C(N(CC)CC)C>O1CCCC1>[C:31]([C:30]1[CH:35]=[CH:36][C:27]([CH2:26][NH:25][C:13](=[O:23])[CH:14]=[CH:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:28][CH:29]=1)([OH:33])=[O:32]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 87842-Propenoic acid, 3-phenyl-HCID 682631,1'-CarbonyldiimidazoleHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochloride

生成物 1

HCID 54481087HCID 54481087、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1,1'-Carbonyldiimidazole (3.71 9) is added to an ice-cold stirred solution of cinnamic acid (3.13 9) in 30 mL tetrahydrofuran. After stirring for an additional 1 hr, methyl 4-(aminomethyl)benzoate hydrochloride (4.7 9) and triethylamine (3.23 mL) are added and the final mixture stirred while immersed in an ice water bath for an additional 30 min, followed by stirring overnight at room temperature. After removal of the solvent by rotary evaporation, the residue is taken up in chloroform (250 mL) and extracted with water (200 mL), 1 N HCl (3×50 mL), water (100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL) and the final chloroform layer dried over anhydrous magnesium sulfate. After evaporation of the solvent in vacuo, the crude product (2.74 g) is suspended in 100 mL tetrahydrofuran and 20 mL 2 N NaOH and the mixture stirred at room temperature overnight. The mixture is then made acidic by addition of excess 1 N HCl, and the precipitate recovered by filtration. After washing the filter cake with water and pressing to remove as much water as possible, the white solid is crystallized from methanol/2N HCl as N-(4-carboxybenzyl)cinnamamide, m.p. 238°-239° C.

後処理

  1. waitwhile immersed in an ice water bath for an additional 30 min
  2. stirringby stirring overnight at room temperature
  3. customAfter removal of the solvent
  4. customby rotary evaporation
  5. extractionextracted with water (200 mL), 1 N HCl (3×50 mL), water (100 mL), saturated sodium bicarbonate (100 mL), brine (100 mL)
  6. dry with materialthe final chloroform layer dried over anhydrous magnesium sulfate
  7. customAfter evaporation of the solvent in vacuo
  8. stirring20 mL 2 N NaOH and the mixture stirred at room temperature overnight
  9. additionmade acidic by addition of excess 1 N HCl
  10. filtrationthe precipitate recovered by filtration
  11. washAfter washing the filter cake with water
  12. customto remove as much water as possible, the white solid
  13. customis crystallized from methanol/2N HCl as N-(4-carboxybenzyl)cinnamamide, m.p. 238°-239° C.

出典と根拠

ORDレコード
ord-4150fa25ce5b45f39c1f064b6b5c337e
出典データセット
uspto-grants-1991_03
特許番号
US05002703

関連ノート

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