Dibutyl squarate → 3-Butoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 1956701Notes

Reaction equation

HRID 1956701 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.[NH2:17][CH:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:19]>O1CCCC1>[CH2:11]([O:10][C:9]1[C:8](=[O:15])[C:7](=[O:16])[C:6]=1[NH:17][CH:18]([CH3:19])[C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 65108Dibutyl squarateHCID 5209072-Butanamine, 3,3-dimethyl-

Product 1

HCID 541350113-Butoxy-4-(1,2,2-trimethyl-propylamino)-cyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (15 mL), 3,4-dibutoxy-3-cyclobutene-1,2-dione (2.26 g, 10 mmol) and 2-amino-3,3-dimethylbutane (1.01 g, 10 mmol) were stirred together for approximately 65 hours at room temperature. The waxy solid remaining after removal of solvent was dissolved in chloroform (15 mL) and chromatographed (flash, ethyl acetate/hexane) on silica. The appropriate fractions were freed of solvent to yield 2.41 g (95%) of cream-colored waxy solid: mp 90°-9° C.° (softens 85° C.).

Workup

  1. customafter removal of solvent
  2. dissolutionwas dissolved in chloroform (15 mL)
  3. customchromatographed (flash, ethyl acetate/hexane) on silica
  4. customto yield 2.41 g (95%) of cream-colored waxy solid
  5. custommp 90°-9° C.° (softens 85° C.)

Sources & evidence

ORD record
ord-84e32d30b63644d1bd43edc9c6aae857
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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