Diethyl squarate → HCID 58736381, compound

HRID 1528182Notes

Reaction equation

HRID 1528182 reaction equation
[NH2:1][C:2]1[C:3]([OH:14])=[C:4]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:15]([O:17][C:18]1[C:19](=O)[C:20](=[O:25])[C:21]=1[O:22]CC)C>CO>[OH:14][C:3]1[C:2]([NH:1][C:19]2[C:20](=[O:25])[C:21](=[O:22])[C:18]=2[O:17][CH3:15])=[CH:7][CH:6]=[CH:5][C:4]=1[S:8]([N:11]([CH3:12])[CH3:13])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 123228Diethyl squarateHCID 207957463-Amino-2-hydroxy-N,N-dimethylbenzene-1-sulfonamide

Product 1

HCID 58736381HCID 58736381, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.94 g (4.10 mmol) of 3-amino-2-hydroxy-N,N-dimethylbenzenesulfonamide and 2.47 g (17.40 mmol) of 3,4-diethoxycyclobut-3-ene-1,2-dione in 20 ml of methanol was stirred at ambient temperature for 4 days. The reaction medium was concentrated. The residue (3.29 g) was chromatographed on silica gel (200 g prepacked column, 100 ml/min, eluent heptane/ethyl acetate, from 50% to 85% of ethyl acetate). 0.86 g of product was obtained in the form of a yellow solid. Yield=64%.

Workup

  1. concentrationThe reaction medium was concentrated
  2. customThe residue (3.29 g) was chromatographed on silica gel (200 g prepacked column, 100 ml/min, eluent heptane/ethyl acetate, from 50% to 85% of ethyl acetate)

Sources & evidence

ORD record
ord-5ebce305acea4e8aba705ff7499d8abd
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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