4-Aminobenzoic Acid → 4-(Cyclohexanecarboxamido)benzoic acid

HRID 401680ノート

反応式

HRID 401680 の反応式
NC1C=CC(C(O)=O)=CC=1.C1(C(Cl)=O)CCCCC1.CCN(CC)CC.[OH-].[Na+].[CH:29]1([C:35]([NH:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([O:44]C)=[O:43])=[CH:40][CH:39]=2)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>C1COCC1>[CH:29]1([C:35]([NH:37][C:38]2[CH:47]=[CH:46][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=2)=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

参加物

7

反応物 5

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 4400321HCID 4400321、化合物

生成物 1

HCID 7457334-(Cyclohexanecarboxamido)benzoic acid収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-aminobenzoic acid 48a (1.98 mmol, 300 mg), cyclohexanecarbonyl chloride 48b (1.98 mmol, 291 mg), and Et3N (2.52 mmol, 0.43 mL) in 6 mL of THF was stirred at room temperature overnight. 1N aqueous NaOH (7.9 mmol, 7.9 mL) was added to the mixture (containing methyl 4-(cyclohexanecarboxamido)benzoate 48c) and the reaction mixture was stirred for 5 h at room temperature. The THF was removed by rotary evaporation and 1N aqueous HCl was added to precipitate the product, which was filtered to give 480 mg (92%) of 48d.

後処理

  1. stirringthe reaction mixture was stirred for 5 h at room temperature
  2. customThe THF was removed by rotary evaporation and 1N aqueous HCl
  3. additionwas added
  4. customto precipitate the product, which
  5. filtrationwas filtered

出典と根拠

ORDレコード
ord-e9e174add9564bfe96df4e03afc70d8f
出典データセット
uspto-grants-2014_06
特許番号
US08741887B2

反応ノート

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