3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → HCID 178493669, compound

HRID 1528185Notes

Reaction equation

HRID 1528185 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:10])[C:4]=2[N:3]=[N:2]1.[CH3:11][O:12][C:13]1[C:14](=O)[C:15](=[O:19])[C:16]=1[O:17]C>CO>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH:10][C:14]3[C:15](=[O:19])[C:16](=[O:17])[C:13]=3[O:12][CH3:11])[C:4]=2[NH:3][N:2]=1

Participants

4

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 178507462HCID 178507462, compound

Product 1

HCID 178493669HCID 178493669, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.045 g (15.2 mmol, 1 eq) of 1H-1,2,3-benzotriazol-4-amine and 1.80 g (12.7 mmol, 1 eq) of 3,4-dimethoxy-3-cyclobutene-1,2-dione in 30 ml of methanol was stirred at ambient temperature for 2 days. The reaction medium (set solid) was filtered. 2.04 g of a mixture of 3-(3H-benzotriazol-4-ylamino)-4-methoxycyclobut-3-ene-1,2-dione and 3,4-bis(3H-benzotriazol-4-ylamino)cyclobut-3-ene-1,2-dione were obtained in the form of a yellow solid. Mixture of products (29% correct product). Yield=19%.

Workup

  1. filtrationThe reaction medium (set solid) was filtered

Sources & evidence

ORD record
ord-3dde3356fb8d447a819a9e6d2e2ca4b0
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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