2,4-Dichlorobenzylamine → 3-(2,4-Dichlorobenzylamino)-4-(1,2,2-trimethylproylamino)-cyclobut-3-ene-1,2-dione

HRID 963448Notes

Reaction equation

HRID 963448 reaction equation
C(O[C:6]1[C:7](=[O:18])[C:8](=[O:17])[C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([CH3:15])([CH3:14])[CH3:13])CCC.[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23]>O1CCCC1>[Cl:19][C:20]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:21]=1[CH2:22][NH:23][C:6]1[C:7](=[O:18])[C:8](=[O:17])[C:9]=1[NH:10][CH:11]([CH3:16])[C:12]([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 14852,4-DichlorobenzylamineHCID 541350113-Butoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 190824393-(2,4-Dichlorobenzylamino)-4-(1,2,2-trimethylproylamino)-cyclobut-3-ene-1,2-dioneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (10 mL), 3-butoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1.01 g, 3.99 mmol, Example 1) and 2,4-dichlorobenzylamine (0.70 g, 4.0 mmol) were stirred together at room temperature for 14 hours. Following removal of solvent, the residue was triturated with diethyl ether and dried. The off-white solid product was recrystallized twice from nitromethane to yield 0.408 g (29%) of the title compound as a white solid: mp 234°-235° C.; 1H NMR: (DMSO-d6): δ 7.67 (m, br, 1H), 7.65 (m, br, 1H), 7.48 (m, 2H), 7.32 (m, br, 1H), 4.80 (m, 2H), 3.90 (m, 1H), 1.10 (d, 3H), 0.86 (s, 9H) ppm. IR (KBr): 3140, 1790, 1640 cm-1 ; MS (m/z): 354/356/358. HPLC indicates a major component (99%).

Workup

  1. customremoval of solvent
  2. customthe residue was triturated with diethyl ether
  3. customdried
  4. customThe off-white solid product was recrystallized twice from nitromethane

Sources & evidence

ORD record
ord-38a901a6f98d49ccb8c1551a3223aea0
Source dataset
uspto-grants-1998_06
Patent number
US05763474

Reaction notes

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