Benzenemethanamine, 3,4-dichloro- → 3-tert-Butylamino-4-(3,4-dichlorobenzylamino)-cyclobut-3-ene-1,2-dione

HRID 963454ノート

反応式

HRID 963454 の反応式
C(O[C:6]1[C:7](=[O:16])[C:8](=[O:15])[C:9]=1[NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])CCC.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[Cl:26])[CH2:21][NH2:22]>O1CCCC1>[C:11]([NH:10][C:9]1[C:8](=[O:15])[C:7](=[O:16])[C:6]=1[NH:22][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([Cl:26])=[C:18]([Cl:17])[CH:19]=1)([CH3:12])([CH3:13])[CH3:14]

参加物

4

反応物 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 178193893-Butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione

生成物 1

HCID 190824213-tert-Butylamino-4-(3,4-dichlorobenzylamino)-cyclobut-3-ene-1,2-dione収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione (1.13 g, 5 mmol, Example 10) and 3,4-dichlorobenzylamine (0.880 g, 5.0 mmol) in tetrahydrofuran (15 mL) was stirred at room temperature for approximately 96 hours. The residue isolated after removal of solvent was recrystallized from N,N-dimethylformamide (twice) and from 2-methoxyethanol to provide 0.687 g (42%) of the title compound as a white solid: mp 302°-303° C.; 1H NMR (DMSO-d6) δ 7.77 (m, 1H), 7.65 (d, 1H), 7.62 (d, 1H), 7.55 (s, 1H), 7.33 (m, 1H), 4.71 (d, 2H), 1.35 (s, 9H) ppm. IR (KBr): 3450, 3230, 1800, 1650 cm-1. MS (m/z) 326/328/330 (M+). HPLC indicates a major component (>99%).

後処理

  1. customThe residue isolated
  2. customafter removal of solvent
  3. customwas recrystallized from N,N-dimethylformamide (twice) and from 2-methoxyethanol

出典と根拠

ORDレコード
ord-a66be46551a941f9a89f754a0a312f09
出典データセット
uspto-grants-1998_06
特許番号
US05763474

反応ノート

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