3-Amino-4-methoxycyclobut-3-ene-1,2-dione → HCID 13505506, compound

HRID 364992Notes

Reaction equation

HRID 364992 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[S:11][CH2:12][CH2:13][NH2:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:18][C:19]1[C:22](=[O:23])[C:21](=[O:24])[C:20]=1OC>CO>[NH2:18][C:19]1[C:22](=[O:23])[C:21](=[O:24])[C:20]=1[NH:14][CH2:13][CH2:12][S:11][C:10]1[CH:15]=[CH:16][CH:17]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1

Participants

4

Reactant 2

HCID 134522053-Amino-4-methoxycyclobut-3-ene-1,2-dioneHCID 135188252-(3-Piperidinomethylthiophenoxy)ethylamine

Product 1

HCID 13505506HCID 13505506, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The crude amine prepared in Step E (1.4 g, 4.05 mmoles) in 40 mL of methanol was added to a suspension of 1-amino-2-methoxycyclobutene-3,4-dione (0.515 g, 4.05 mmoles) in 100 mL of methanol. The mixture was stirred for 20 hours at ambient temperature and then filtered to give 0.8136 g of product. A second crop was obtained from the concentrated mother liquor and the combined lots were recrystallized from methanol to yield 0.786 g (56%) of the title compound, m.p. 228°-230° (dec.).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-63a7d783e29441c19d9b42ff926bf178
Source dataset
uspto-grants-1986_08
Patent number
US04607105

Reaction notes

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