Benzenemethanamine, 3,5-dichloro- → 3-(3,5-Dichloro-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 1956725Notes

Reaction equation

HRID 1956725 reaction equation
C(O[C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])CCC.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH2:22][NH2:23]>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH2:22][NH:23][C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:14])([CH3:15])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 457602Benzenemethanamine, 3,5-dichloro-HCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 537856713-(3,5-Dichloro-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dioneYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5 mmol, Example 3), 3,5-dichlorobenzylamine (0.88 g, 5 mmol) and tetrahydrofuran (15 mL) was stirred at room temperature for 3 days. The reaction mixture was processed as in Example 2, Step 4. The crude product was recrystallized (twice) from methanol to provide 1.309 g of the title compound as a white solid: mp 257°-258° C. (dec). MS (m/z) 340/342/344 (M+). HPLC indicates a major component (97%).

Workup

  1. customThe crude product was recrystallized (twice) from methanol

Sources & evidence

ORD record
ord-61cf12a47c924c7bb2645d5ec574f919
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

Loading…