Tert-Butylamine → 3-Tert-butylamino-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione

HRID 357299Notes

Reaction equation

HRID 357299 reaction equation
C(O[C:4]1[C:5](=[O:18])[C:6](=[O:17])[C:7]=1[NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:16])C.[C:19]([NH2:23])([CH3:22])([CH3:21])[CH3:20]>ClCCl>[C:19]([NH:23][C:4]1[C:5](=[O:18])[C:6](=[O:17])[C:7]=1[NH:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:16])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 189374263-Ethoxy-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione

Product 1

HCID 189374243-Tert-butylamino-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethoxy-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione (0.4 g, 1.62mmol) in t-butylamine (4.8mL) and dichloromethane (4.8mL) was allowed to stand at room temperature for 7 days. The slurry was filtered, rinsed with ethyl acetate, and dried. Chromatography with 10% methanol in dichloromethane, followed by trituration with 5% ethyl acetate in hexane gave 3-tert-butylamino-4-(2-hydroxy-6-methyl-phenylamino)-cyclobut-3-ene-1,2-dione, 0.18 g (0.66 mmol, 41%).

Workup

  1. filtrationThe slurry was filtered
  2. washrinsed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-983ce19afacc4131a286782490bdc505
Source dataset
uspto-grants-1998_11
Patent number
US05840764

Reaction notes

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