Triethylamine → 3-tert-Butylamino-4-(2,6-dichloro-benzylamino)-cyclobut-3-ene-1,2-dione

HRID 1956707Notes

Reaction equation

HRID 1956707 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.C([O:23][C:24]1[C:25](=[O:34])[C:26](=O)[C:27]=1[NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])CCC>O1CCCC1>[C:29]([NH:28][C:27]1[C:24](=[O:23])[C:25](=[O:34])[C:26]=1[NH:6][CH2:5][C:4]1[C:3]([Cl:2])=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:11])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16644432(2,6-Dichlorophenyl)methanamine hydrochlorideHCID 178193893-Butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione

Product 1

HCID 105922813-tert-Butylamino-4-(2,6-dichloro-benzylamino)-cyclobut-3-ene-1,2-dioneYield 38.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2,6-dichlorobenzylamine hydrochloride from Example 5, Step 2 (1.06 g, 5.0 mmol) in tetrahydrofuran (10 mL ) was added triethylamine (0.505 g, 5.0 mmol) followed by 3-butoxy-4-tert-butylamino-cyclobut-3-ene-1,2-dione (1.13 g, 5.0 mmol, Example 1) and stirring was continued for approximately 16 hours. The reaction mixture was freed of solvent and the residue was triturated with water, with diethyl ether and dried. The white solid thus isolated was crystallized twice from methanol to give 0.623 g (38%) of the title compound as a white solid: mp 265°-6° C. dec (softens 263° C.); 1H NMR (DMSO-d6) δ7.55 (d, 2H), 7.49 (br m, 1H), 7.42 (m, 2H), 5.05 (d, 2H), 1.34 (s, 9H) ppm. IR (KBr): 3185, 1785, 1660 cm-1 ; MS (m/z) 326/328/330 (M+). HPLC indicates a major component (99.9%).

Workup

  1. customthe residue was triturated with water, with diethyl ether
  2. customdried
  3. customThe white solid thus isolated
  4. customwas crystallized twice from methanol

Sources & evidence

ORD record
ord-94d7a23fc8fc461e842f2c8469b5317d
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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