3-Cyclobutene-1,2-dione, 3,4-dimethoxy- → HCID 178493688, compound

HRID 1528192Notes

Reaction equation

HRID 1528192 reaction equation
[NH2:1][C:2]1[C:3]([OH:10])=[C:4]([C:7]([O-:9])=[O:8])[S:5][CH:6]=1.[CH3:11][N-:12][CH3:13].[CH3:14][O:15][C:16]1[C:17](=O)[C:18](=[O:22])[C:19]=1[O:20]C>CO>[OH:10][C:3]1[C:2]([NH:1][C:17]2[C:18](=[O:22])[C:19](=[O:20])[C:16]=2[O:15][CH3:14])=[CH:6][S:5][C:4]=1[C:7]([O-:9])=[O:8].[CH3:11][N-:12][CH3:13]

Participants

4

Reactant 2

HCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-HCID 178484926HCID 178484926, compound

Product 1

HCID 178493688HCID 178493688, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5.20 g (27.92 mmol, 1.0 eq) of dimethylamide 4-amino-3-hydroxythiophene-2-carboxylate and 5.95 g (41.88 mmol, 1.5 eq) of 3,4-dimethoxy-3-cyclobutene-1,2-dione in 52 ml of methanol was heated at 50° C. for 16 hours. The insoluble material was filtered off and oven-dried under vacuum at 45° C. 7.38 g of dimethylamide 3-hydroxy-4-(2-methoxy-3,4-dioxocyclobut-1-enylamino)thiophene-2-carboxylate were obtained. Yield=89%.

Workup

  1. filtrationThe insoluble material was filtered off
  2. customoven-dried under vacuum at 45° C

Sources & evidence

ORD record
ord-fec6427fa78a449c9bd5f4ea7136e38a
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

Loading…