2,4-Dimethylbenzylamine → 3-tert-Butylamino-4-(2,4-dimethyl-benzylamino)-cyclobut-3-ene-1,2-dione

HRID 1956705

反応式

HRID 1956705 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.[CH3:17][C:18]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>O1CCCC1>[C:11]([NH:10][C:9]1[C:8](=[O:15])[C:7](=[O:16])[C:6]=1[NH:21][CH2:20][C:19]1[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]=1[CH3:17])([CH3:12])([CH3:13])[CH3:14]

参加物

4

反応物 2

HCID 667612,4-DimethylbenzylamineHCID 178193893-Butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione

生成物 1

HCID 107556543-tert-Butylamino-4-(2,4-dimethyl-benzylamino)-cyclobut-3-ene-1,2-dione収率 47%

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, 5.0 mmol, Example 1) and 2,4-dimethylbenzylamine (0.68 g, 5.0 mmol, a mixture of 2,4- and 2,6-dimethylbenzylamine isomers) in tetrahydrofuran (10 mL) was stirred at room temperature for approximately 16 hours. Removal of solvent, thorough trituration of the residue with diethyl ether and drying provided 1.07 g of crude product. Three recrystallizations of this material from acetonitrile gave 0.67 g (47%) of the title compound as a white solid: mp 228°-229° C.; 1H NMR (DMSO-d6) δ7.57 (m, 1H), 7.48 (s, br, 1H), 7.17 (d, 1H), 7.03 (s, br, 1H), 7.00 (d, br, 1H), 4.69 (d, 2H), 2.27 (s, 3H), 2.24 (s, 3H), 1.35 (s, 9H) ppm. IR (KBr): 3310, 1785, 1670 cm-1 ; MS (m/z) 286 (M+). HPLC indicates a major component (98.7%).

後処理

  1. customRemoval of solvent, thorough trituration of the residue with diethyl ether
  2. customdrying
  3. customprovided 1.07 g of crude product
  4. customThree recrystallizations of this material from acetonitrile

出典と根拠

ORDレコード
ord-4f411219929b46dda98a7678a89f73d9
出典データセット
uspto-grants-1998_07
特許番号
US05780505

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