4-Chloroaniline → HCID 23434032, compound

HRID 885121Notes

Reaction equation

HRID 885121 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 on 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 on SiO2 gel
  4. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c81fb7368bd046808214548a4b78c0bd
Source dataset
uspto-grants-2012_08
Patent number
US08242139B2

Reaction notes

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