2,3-Dichlorobenzylamine → HCID 54225953, compound

HRID 1956731Notes

Reaction equation

HRID 1956731 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[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22]>O1CCCC1>[Cl:18][C:19]1[C:26]([Cl:27])=[CH:25][CH:24]=[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 5876252,3-DichlorobenzylamineHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 54225953HCID 54225953, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (12 mL), 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5.0 mmol) and 2,3-dichlorobenzylamine (0.88 g, 5.0 mmol) were stirred together at room temperature for 64 hours. The residue remaining after removal of solvent was trituated thoroughly with diethyl ether and dried to give 1.55 g of a white solid. Recrystallization (four times) of the crude product from acetonitrile provided 0.796 g of the title compound as a white solid: mp 222°-223° C. (softens 218° C.). MS (m/z) 340/342/344 (M+). HPLC indicates a major component (96.2%).

Workup

  1. customafter removal of solvent
  2. customdried

Sources & evidence

ORD record
ord-149711fdd8684b3399c3ee0eb6c9b062
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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