Triethylamine → 3-(1,1-Dimethyl-propylamino)-4-(2,4,6-trimethyl-benzylamino)-cyclobut-3-ene-1,2-dione

HRID 1956721Notes

Reaction equation

HRID 1956721 reaction equation
C(O[C:6]1[C:7](=[O:17])[C:8](=[O:16])[C:9]=1[NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][CH3:13])CCC.Cl.[CH3:19][C:20]1[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:21]=1[CH2:22][NH2:23].C(N(CC)CC)C>O1CCCC1>[CH3:15][C:11]([NH:10][C:9]1[C:8](=[O:16])[C:7](=[O:17])[C:6]=1[NH:23][CH2:22][C:21]1[C:20]([CH3:19])=[CH:27][C:26]([CH3:28])=[CH:25][C:24]=1[CH3:29])([CH3:14])[CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458432(2,4,6-Trimethylphenyl)methanamine hydrochlorideHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 104954903-(1,1-Dimethyl-propylamino)-4-(2,4,6-trimethyl-benzylamino)-cyclobut-3-ene-1,2-dioneYield 42.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrahydrofuran (15 mL), 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1,20 g, 5 mmol), 2,4,6-trimethylbenzylamine hydrochloride (0.928 g, 5 mmol, Example 9, Step 2) and triethylamine (0.506 g, 5 mmol) were stirred together at room temperature for 3 days. The mixture was then prepared as in Example 9, Step 3. Three recrystallization of the crude product from acetonitrile provided 0.664 g of the title compound as a white solid: mp 284°-5° C. (dec) (softens 282° C.). MS (m/z) 314 (M+).

Workup

  1. customThe mixture was then prepared as in Example 9, Step 3
  2. customThree recrystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-a74bd2805e124a75b5371431db41b9e6
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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