4-Chloroaniline → HCID 23434032, compound

HRID 1397493Notes

Reaction equation

HRID 1397493 reaction equation
C(O[C:4]1[C:5](=[O:12])[C:6](=[O:11])[C:7]=1[O:8][CH2:9][CH3:10])C.[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C(O)C>[Cl:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:4]2[C:5](=[O:12])[C:6](=[O:11])[C:7]=2[O:8][CH2:9][CH3:10])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 123228Diethyl squarate

Product 1

HCID 23434032HCID 23434032, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a refluxing solution of 3,4-diethoxycyclobut-3-ene-1,2-dione (1.05 g, 6.14 mmol) in ethanol (25 mL) was added an ethanol (10 mL) solution of 4-chloroaniline (0.784 g, 6.14 mmol) by syringe pump over 2 h. The heating bath was removed, and the reaction stirred at room temperature for 16 h. The reaction was concentrated under reduced pressure and purified by chromatography oh SiO2 gel, eluting with 50% ethyl acetate in hexane to give the title compound. MS (ESI) m/z 252 [M+H]+.

Workup

  1. customThe heating bath was removed
  2. concentrationThe reaction was concentrated under reduced pressure
  3. custompurified by chromatography oh SiO2 gel
  4. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-72361dbde07747e49fbdc579d82c9d89
Source dataset
uspto-grants-2014_12
Patent number
US08901152B2

Reaction notes

Loading…