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

HRID 1956724Notes

Reaction equation

HRID 1956724 reaction equation
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:19]=[C:20]([CH:23]=[CH:24][C:25]=1[CH3:26])[CH2:21][NH2:22]>O1CCCC1>[C:11]([NH:10][C:9]1[C:8](=[O:15])[C:7](=[O:16])[C:6]=1[NH:22][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([CH3:26])=[C:18]([CH3:17])[CH:19]=1)([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 66888Benzenemethanamine, 3,4-dimethyl-HCID 178193893-Butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione

Product 1

HCID 178193593-tert-Butylamino-4-(3,4-dimethyl-benzylamino)-cyclobut-3-ene-1,2-dioneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (17 mL), 3-butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione (1.13 g, 5 mmol, Example 1) and 3,4-dimethylbenzylamine (0.68 g, 5 mmol) were stirred together at room temperature for 2 days. Removal of solvent and trituration of the residue with diethyl ether gave 1.06 g of a light yellow solid. Four recrystallizations of this material from acetonitrile provided 0.394 g of the tide compound as a white solid: mp 264°-264° C. (softens 260° C.). MS (m/z) 286 (M+). HPLC indicates a major component (96%).

Workup

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

Sources & evidence

ORD record
ord-0c7ee9d1b05c4af49afe65479a181b9d
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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