Triethylamine → HCID 15537968、化合物

HRID 1836924ノート

反応式

HRID 1836924 の反応式
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[S:3]1.C(N(CC)CC)C.C(Cl)(=O)OCC.[N+:33]([C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1)([O-:35])=[O:34]>C(Cl)Cl>[N+:33]([C:36]1[CH:37]=[CH:38][C:39]([CH2:40][NH:41][C:14](=[O:16])[C:13]2[CH:17]=[C:9]([CH2:8][CH:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])[CH:10]=[CH:11][C:12]=2[O:18][CH3:19])=[CH:42][CH:43]=1)([O-:35])=[O:34]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 291474-NitrobenzylamineHCID 9943613HCID 9943613、化合物

生成物 1

HCID 15537968HCID 15537968、化合物収率 75.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid (422 mg, 1.50 mmol), triethylamine (0.732 mL, 5.25 mmol) and methylene chloride (7 mL) were mixed and ethyl chlorocarbonate (0.158 mL, 1.50 mmol) was added under cooling with ice and stirring. After stirring for 10 minutes under cooling with ice, 4-nitrobenzylamine (283 mg, 1.50 mmol) was added. The mixture was stirred for 2 hours at room temperature, and then allowed to stand overnight. After washed with water, the reaction mixture was dried over anhydrous sodium sulfate and concentrated. The residue was dissolved into water (20 mL), which was made acidic with 10% hydrochloric acid and stirred for 2 hours. The precipitated crystals were collected by filtration, washed with water and dried, then they were recrystallized from ethanol to obtain 472 mg (75%) of the title compound as pale yellow prisms.

後処理

  1. temperatureunder cooling with ice
  2. stirringAfter stirring for 10 minutes
  3. additionwas added
  4. stirringThe mixture was stirred for 2 hours at room temperature
  5. washAfter washed with water
  6. dry with materialthe reaction mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved into water (20 mL), which
  9. stirringstirred for 2 hours
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with water
  12. customdried
  13. customthey were recrystallized from ethanol

出典と根拠

ORDレコード
ord-be7dd842e84346eb98926c17b8bc24d6
出典データセット
uspto-grants-2004_08
特許番号
US06780431B1

反応ノート

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