Benzenemethanamine, 2,5-dichloro- → HCID 18663648, compound

HRID 1956723Notes

Reaction equation

HRID 1956723 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:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:20]=1[CH2:21][NH2:22]>O1CCCC1>[Cl:18][C:19]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:20]=1[CH2:21][NH:22][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 457600Benzenemethanamine, 2,5-dichloro-HCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 18663648HCID 18663648, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (13 mL), 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5 mmol) and 2,5-dichlorobenzylamine (0.88 g, 5 mmol) were stirred together for approximately 64.5 hours. Removal of solvent and thorough trituration of the residue with diethyl ether gave 1.51 g of a light yellow solid. As purification of this material by three recrystallizations from acetonitrile was unrewarding, the recovered crude product was subjected to HPLC. The solid isolated from the appropriate fractions was recrystallized from acetonitrile to afford 0.598 g of the title compound as a white solid: mp 195°-196° C. MS (m/z) 340/342/344 (M+). HPLC indicates a major component (>99%).

Workup

  1. customRemoval of solvent and thorough trituration of the residue with diethyl ether

Sources & evidence

ORD record
ord-c840f79d903d4eb495e39675f8905d9a
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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