Dibutyl squarate → 4-[(2-Butoxy-3,4-dioxo-cyclobut-1-enylamino)-methyl]-3-chloro-benzonitrile

HRID 1956727Notes

Reaction equation

HRID 1956727 reaction equation
C(O[C:6]1[C:7](=[O:16])[C:8](=[O:15])[C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14])CCC.[Cl:17][C:18]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>O1CCCC1>[CH2:11]([O:10][C:9]1[C:8](=[O:15])[C:7](=[O:16])[C:6]=1[NH:21][CH2:20][C:19]1[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:18]=1[Cl:17])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 65108Dibutyl squarateHCID 40897884-(Aminomethyl)-3-chlorobenzonitrile

Product 1

HCID 186636514-[(2-Butoxy-3,4-dioxo-cyclobut-1-enylamino)-methyl]-3-chloro-benzonitrileYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4-dibutoxy-3-cyclobutene-1,2-dione (2.263 g, 10 mmol) and 2-chloro-4-cyanobenzylamine (1.666 g, 10 mmol, Example 2, Step 3) in tetrahydrofuran (25 mL) was stirred at room temperature for 22 hours. The residue remaining after removal of solvent was dissolved in chloroform and was chromatographed (flash, ethyl acetate/hexane) on silica. The solid isolated from the appropriate fractions was recrystallized from ethyl acetate to provide 2.427 g of a white solid: mp 147.5°-149° C. MS (m/z) 318 (M+). HPLC indicates a major component (>99%).

Workup

  1. customafter removal of solvent
  2. dissolutionwas dissolved in chloroform
  3. customwas chromatographed (flash, ethyl acetate/hexane) on silica
  4. customThe solid isolated from the appropriate fractions
  5. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-092e034e3fea4be18cbffa58b0f5b4e7
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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